JP6877665B1 - Antiviral agent composition and antiviral fabric, antiviral polyurethane sheet and antiviral polyvinyl chloride sheet treated with the composition. - Google Patents
Antiviral agent composition and antiviral fabric, antiviral polyurethane sheet and antiviral polyvinyl chloride sheet treated with the composition. Download PDFInfo
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- JP6877665B1 JP6877665B1 JP2021018415A JP2021018415A JP6877665B1 JP 6877665 B1 JP6877665 B1 JP 6877665B1 JP 2021018415 A JP2021018415 A JP 2021018415A JP 2021018415 A JP2021018415 A JP 2021018415A JP 6877665 B1 JP6877665 B1 JP 6877665B1
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- antiviral
- antiviral agent
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- 239000003443 antiviral agent Substances 0.000 title claims abstract description 123
- 239000000203 mixture Substances 0.000 title claims abstract description 113
- 239000004744 fabric Substances 0.000 title claims abstract description 60
- 239000004814 polyurethane Substances 0.000 title claims abstract description 53
- 230000000840 anti-viral effect Effects 0.000 title claims abstract description 52
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 52
- 239000004800 polyvinyl chloride Substances 0.000 title claims abstract description 30
- 229920000915 polyvinyl chloride Polymers 0.000 title claims abstract description 30
- -1 methoxysilane quaternary ammonium salt Chemical class 0.000 claims abstract description 69
- 229920005749 polyurethane resin Polymers 0.000 claims abstract description 39
- 239000011230 binding agent Substances 0.000 claims abstract description 35
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 34
- 229920000570 polyether Polymers 0.000 claims abstract description 21
- 150000007942 carboxylates Chemical group 0.000 claims abstract description 20
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 19
- 239000002270 dispersing agent Substances 0.000 claims abstract description 18
- 229920000620 organic polymer Polymers 0.000 claims abstract description 10
- 229920005989 resin Polymers 0.000 claims description 30
- 239000011347 resin Substances 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 22
- 239000000463 material Substances 0.000 claims description 12
- 239000000230 xanthan gum Substances 0.000 claims description 11
- 229920001285 xanthan gum Polymers 0.000 claims description 11
- 235000010493 xanthan gum Nutrition 0.000 claims description 11
- 229940082509 xanthan gum Drugs 0.000 claims description 11
- 239000004925 Acrylic resin Substances 0.000 claims description 10
- 229920000178 Acrylic resin Polymers 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 5
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 claims description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 3
- 239000001856 Ethyl cellulose Substances 0.000 claims description 3
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims description 3
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 3
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 3
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 3
- 229920002472 Starch Polymers 0.000 claims description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 3
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 3
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 3
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- 235000019325 ethyl cellulose Nutrition 0.000 claims description 3
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 3
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 3
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 3
- 229920000609 methyl cellulose Polymers 0.000 claims description 3
- 239000001923 methylcellulose Substances 0.000 claims description 3
- 235000010981 methylcellulose Nutrition 0.000 claims description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 3
- 239000008107 starch Substances 0.000 claims description 3
- 235000019698 starch Nutrition 0.000 claims description 3
- 238000012545 processing Methods 0.000 abstract description 14
- 238000010586 diagram Methods 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 54
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 45
- 239000010410 layer Substances 0.000 description 39
- 239000007788 liquid Substances 0.000 description 39
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 29
- 229920005862 polyol Polymers 0.000 description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 238000000034 method Methods 0.000 description 22
- 150000003077 polyols Chemical class 0.000 description 22
- 125000004432 carbon atom Chemical group C* 0.000 description 21
- 239000006185 dispersion Substances 0.000 description 21
- 239000005056 polyisocyanate Substances 0.000 description 21
- 229920001228 polyisocyanate Polymers 0.000 description 21
- 239000012948 isocyanate Substances 0.000 description 17
- 150000002513 isocyanates Chemical group 0.000 description 17
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 16
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 16
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000000839 emulsion Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 14
- 239000004417 polycarbonate Substances 0.000 description 14
- 229920000515 polycarbonate Polymers 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 229920000768 polyamine Polymers 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 238000011156 evaluation Methods 0.000 description 12
- 150000002430 hydrocarbons Chemical group 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 11
- 238000011161 development Methods 0.000 description 11
- 238000001035 drying Methods 0.000 description 11
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 10
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 9
- 239000000835 fiber Substances 0.000 description 9
- 238000006386 neutralization reaction Methods 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical class NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 8
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 8
- 230000000844 anti-bacterial effect Effects 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 238000007664 blowing Methods 0.000 description 6
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 6
- 238000004945 emulsification Methods 0.000 description 6
- 210000002615 epidermis Anatomy 0.000 description 6
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 210000003491 skin Anatomy 0.000 description 6
- 239000012209 synthetic fiber Substances 0.000 description 6
- 229920002994 synthetic fiber Polymers 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- 239000005977 Ethylene Substances 0.000 description 5
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- 238000005299 abrasion Methods 0.000 description 5
- 239000004840 adhesive resin Substances 0.000 description 5
- 229920006223 adhesive resin Polymers 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 229920005906 polyester polyol Polymers 0.000 description 5
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 5
- 239000002335 surface treatment layer Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- 239000004970 Chain extender Substances 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000002485 combustion reaction Methods 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- 239000003063 flame retardant Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 230000037303 wrinkles Effects 0.000 description 4
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
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- UDSAIICHUKSCKT-UHFFFAOYSA-N bromophenol blue Chemical compound C1=C(Br)C(O)=C(Br)C=C1C1(C=2C=C(Br)C(O)=C(Br)C=2)C2=CC=CC=C2S(=O)(=O)O1 UDSAIICHUKSCKT-UHFFFAOYSA-N 0.000 description 3
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- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical compound CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 description 2
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Abstract
【課題】メトキシシラン系第4級アンモニウム塩を含む抗ウイルス剤と水系ポリウレタン樹脂とを、1回の加工により同浴で付与できる抗ウイルス剤組成物の提供。また、当該抗ウイルス剤組成物を用いて形成された層を表面に有する抗ウイルス性布帛、ポリウレタンシート、ポリ塩化ビニルシートの提供。【解決手段】本発明の抗ウイルス剤組成物は、メトキシシラン系第4級アンモニウム塩を含む抗ウイルス剤と、バインダーとしての、カルボキシル基及び/又はカルボキシレート基を有する水系ポリウレタン樹脂とを含む混合物であって、分散剤として、水溶性有機高分子(例えば、ウレタン変性ポリエーテル等)を含有する。【選択図】なしPROBLEM TO BE SOLVED: To provide an antiviral agent composition capable of applying an antiviral agent containing a methoxysilane quaternary ammonium salt and an aqueous polyurethane resin in the same bath by one processing. Further, the present invention provides an antiviral fabric, a polyurethane sheet, and a polyvinyl chloride sheet having a layer formed by using the antiviral agent composition on the surface. The antiviral agent composition of the present invention is a mixture containing an antiviral agent containing a methoxysilane quaternary ammonium salt and an aqueous polyurethane resin having a carboxyl group and / or a carboxylate group as a binder. However, it contains a water-soluble organic polymer (for example, urethane-modified polyether, etc.) as a dispersant. [Selection diagram] None
Description
本発明は、抗ウイルス剤を含む組成物、および、当該組成物で処理された抗ウイルス性布帛、および当該組成物で表面コートされた抗ウイルス性ポリウレタン(PU)シート、抗ウイルス性ポリ塩化ビニル(PVC)シートに関する。 The present invention comprises a composition containing an antiviral agent, an antiviral fabric treated with the composition, an antiviral polyurethane (PU) sheet surface coated with the composition, and an antiviral polyvinyl chloride. (PVC) Regarding sheets.
近年、環境衛生に対する意識の高まりと関連して、多くの抗菌・抗ウイルス剤や、抗菌・抗ウイルス剤を付与した素材が開発されてきた。ケイ素を含む抗菌剤・抗ウイルス剤として、加水分解可能な基を含むオルガノシラン化合物が公知である。これらの中で、素材の表面に固定化可能な抗ウイルス剤として、エトキシシラン系第4級アンモニウム塩が知られている(特許文献1)。この抗ウイルス剤は、分子中に、抗ウイルス性を発現する比較的長鎖のアルキル基を有するアンモニウム基と、素材の表面と共有結合を形成し得るアルコキシシリル基とを有しており、アルコキシシリル基が、無機材料等の表面に存在するヒドロキシル基等の含酸素官能基と反応し、共有結合を形成することによって、材料の表面に強固に固定化されるという特徴がある。 In recent years, many antibacterial / antiviral agents and materials to which antibacterial / antiviral agents have been added have been developed in connection with increasing awareness of environmental hygiene. As an antibacterial agent / antiviral agent containing silicon, an organosilane compound containing a hydrolyzable group is known. Among these, an ethoxysilane-based quaternary ammonium salt is known as an antiviral agent that can be immobilized on the surface of a material (Patent Document 1). This antiviral agent has an ammonium group having a relatively long-chain alkyl group exhibiting antiviral properties in the molecule and an alkoxysilyl group capable of forming a covalent bond with the surface of the material, and is alkoxy. The silyl group reacts with an oxygen-containing functional group such as a hydroxyl group existing on the surface of an inorganic material or the like to form a covalent bond, so that the silyl group is firmly immobilized on the surface of the material.
一方、前記の抗ウイルス剤を、表面に含酸素官能基を有さない物品、例えばポリエステル繊維等の合成繊維やポリプロピレン等の樹脂材料等に固定化する場合には、前処理の工程が必要とされていた。特許文献1には、物品の表面に含酸素官能基を付与するために、抗ウイルス剤を付与する前に、物品に対してオゾン水処理を行うことも開示されている。 On the other hand, when the antiviral agent is immobilized on an article having no oxygen-containing functional group on its surface, for example, a synthetic fiber such as polyester fiber or a resin material such as polypropylene, a pretreatment step is required. It had been. Patent Document 1 also discloses that an article is treated with ozone water before an antiviral agent is applied in order to impart an oxygen-containing functional group to the surface of the article.
また特許文献2には、合成樹脂の物品に前記の抗ウイルス剤を固定化する場合、抗ウイルス剤の固定化に先立ってプラズマ処理を行うことによって、合成樹脂がポリメタクリル酸メチル樹脂やポリエチレンテレフタレート樹脂である場合にも、抗ウイルス剤を効率的に固定化できることが開示されている。また特許文献3には、上記の抗ウイルス剤を物品の表面に固定化するために、オゾン水処理のほか、マイクロ波照射を行うことが記載されている。オゾン水処理及びマイクロ波照射はいずれも、物品の表面に−OH基や−CHO基(アルデヒド基)、又は−O−基等を生じさせるために行われている。 Further, in Patent Document 2, when the above-mentioned antiviral agent is immobilized on a synthetic resin article, the synthetic resin is made of polymethyl methacrylate resin or polyethylene terephthalate by performing plasma treatment prior to immobilization of the antiviral agent. It is disclosed that the antiviral agent can be efficiently immobilized even when it is a resin. Further, Patent Document 3 describes that in addition to ozone water treatment, microwave irradiation is performed in order to immobilize the above antiviral agent on the surface of an article. Both ozone water treatment and microwave irradiation are performed to generate -OH group, -CHO group (aldehyde group), -O- group, etc. on the surface of the article.
さらに特許文献4には、上記の抗ウイルス剤を合成繊維に固定化するために、抗ウイルス剤の固定化処理に先立って、合成繊維にカルボキシル基を有するバインダーを付与することが開示されている。特許文献4の発明によれば、ポリエステル繊維などの合成繊維等に対して、好適に抗ウイルス剤を付与できる。 Further, Patent Document 4 discloses that, in order to immobilize the above antiviral agent on the synthetic fiber, a binder having a carboxyl group is added to the synthetic fiber prior to the immobilization treatment of the antiviral agent. .. According to the invention of Patent Document 4, an antiviral agent can be suitably applied to synthetic fibers such as polyester fibers.
また、特許文献5には、上記の抗ウイルス剤と特定のアクリル酸系の樹脂成分との相溶性を検証することにより、1回の加工で処理できる方法が開示されている。 Further, Patent Document 5 discloses a method capable of treating by one processing by verifying the compatibility between the above antiviral agent and a specific acrylic acid-based resin component.
上述のとおり、エトキシシラン系第4級アンモニウム塩を物品の表面に固定化するために様々な方法が提案されているが、プラズマ処理を行うためにはプラズマ処理装置が必要となる。また、オゾン水処理やマイクロ波照射を行うためには、それぞれオゾン水を供給する設備や、マイクロ波を発生させるための専用の設備が必要となっていた。
特許文献4では、最初にバインダーの付与、その後に抗ウイルス剤の付与の2回に分けて加工を行うことが必要であり、生産効率やコストを考えた時に不利益であった。
特許文献5では、特定のアクリル酸系の樹脂成分を使用することで相溶性が改善された抗ウイルス剤を含む組成物が開示されているものの、相溶性は不十分であり向上の余地があった。
As described above, various methods have been proposed for immobilizing the ethoxysilane-based quaternary ammonium salt on the surface of the article, but a plasma treatment apparatus is required to perform the plasma treatment. Further, in order to perform ozone water treatment and microwave irradiation, equipment for supplying ozone water and dedicated equipment for generating microwaves are required.
In Patent Document 4, it is necessary to perform the processing in two steps of first adding a binder and then adding an antiviral agent, which is disadvantageous when considering production efficiency and cost.
Patent Document 5 discloses a composition containing an antiviral agent whose compatibility is improved by using a specific acrylic acid-based resin component, but the compatibility is insufficient and there is room for improvement. It was.
この状況に鑑み、本発明は、メトキシシラン系4級アンモニウム塩を含む抗ウイルス剤と、バインダー(ポリウレタン樹脂もしくは、ポリウレタン樹脂とアクリル系樹脂)との相溶性が従来より良好であり、1回の加工にて同浴で付与できる抗ウイルス剤組成物を提供することを課題とする。
さらに、本発明は、抗ウイルス剤が固定化され、抗ウイルス性を有する布帛、ポリウレタンシート、および、ポリ塩化ビニルシートを提供することを課題とする。
In view of this situation, the present invention has better compatibility between the antiviral agent containing the methoxysilane quaternary ammonium salt and the binder (polyurethane resin or polyurethane resin and acrylic resin) than before, and once. An object of the present invention is to provide an antiviral agent composition that can be applied in the same bath by processing.
Furthermore, it is an object of the present invention to provide a cloth, a polyurethane sheet, and a polyvinyl chloride sheet in which an antiviral agent is immobilized and has antiviral properties.
発明者らは、上記課題について検討を進め、抗ウイルス剤として、メトキシシラン系4級アンモニウム塩を含むものを用いることとし、バインダーとして、カルボキシル基及び/又はカルボキシレート基を有する水系ポリウレタン樹脂もしくは、当該ポリウレタン樹脂とアクリル系樹脂の混合物を用いることとした。
そして、バインダーとして、カルボキシル基及び/又はカルボキシレート基を有する水系ポリウレタン樹脂もしくは、当該ポリウレタン樹脂とアクリル系樹脂の混合物を用いた場合、あらかじめ特定の水溶性高分子を添加することで抗ウイルス剤とバインダーの相溶性が良好で、抗ウイルス剤を1回の加工で製品に固着化することが可能で、また、耐久性にも優れた抗菌性および抗ウイルス性を有する布帛、ポリウレタンシート、ポリ塩化ビニルシートを得られることを見出し、本発明を完成した。
The inventors have proceeded with the study on the above-mentioned problems, and decided to use a methoxysilane-based quaternary ammonium salt as an antiviral agent, and as a binder, an aqueous polyurethane resin having a carboxyl group and / or a carboxylate group, or It was decided to use a mixture of the polyurethane resin and the acrylic resin.
When an aqueous polyurethane resin having a carboxyl group and / or a carboxylate group or a mixture of the polyurethane resin and an acrylic resin is used as the binder, an antiviral agent can be obtained by adding a specific water-soluble polymer in advance. Good compatibility of binders, antiviral agents can be fixed to products in one process, and durable antibacterial and antiviral fabrics, polyurethane sheets, polyvinyl chloride We have found that a vinyl sheet can be obtained and completed the present invention.
なお、本明細書中で「カルボキシル基及び/又はカルボキシレート基を有する」とは、組成物中や布帛の表面に存在するカルボキシル基が、解離していないフリーのカルボキシル基(−COOH)として存在する場合だけでなく、末端の水素原子が離脱してカルボキシレートアニオンになっている場合やカルボキシレートアニオンと抗ウイルス剤分子とが化学的に結合している場合も、特に断りのない限り、含むものとする。 In addition, in this specification, "having a carboxyl group and / or a carboxylate group" means that the carboxyl group existing in the composition or on the surface of the cloth exists as a non-dissociated free carboxyl group (-COOH). Unless otherwise specified, the case where the terminal hydrogen atom is detached to become a carboxylate anion or the case where the carboxylate anion and the antiviral agent molecule are chemically bonded is included. It shall be muted.
すなわち、本発明は次の構成を有する。
[1]メトキシシラン系第4級アンモニウム塩を含む抗ウイルス剤と、
バインダーとしての、カルボキシル基及び/又はカルボキシレート基を有する水系ポリウレタン樹脂と、
を含む混合物であって、分散剤として水溶性有機高分子を含有することを特徴とする抗ウイルス剤組成物。
[2]前記バインダーが、カルボキシル基及び/又はカルボキシレート基を有する前記水系ポリウレタン樹脂と、アクリル系樹脂の混合物であることを特徴とする、[1]に記載の抗ウイルス剤組成物。
[3]前記メトキシシラン系第4級アンモニウム塩が、下記式(1)で表される構造の化合物であることを特徴とする、[1]又は[2]に記載の抗ウイルス剤組成物。
That is, the present invention has the following configuration.
[1] An antiviral agent containing a methoxysilane quaternary ammonium salt,
An aqueous polyurethane resin having a carboxyl group and / or a carboxylate group as a binder, and
An antiviral agent composition comprising a water-soluble organic polymer as a dispersant.
[2] The antiviral agent composition according to [1], wherein the binder is a mixture of the aqueous polyurethane resin having a carboxyl group and / or a carboxylate group and an acrylic resin.
[3] The antiviral agent composition according to [1] or [2], wherein the methoxysilane quaternary ammonium salt is a compound having a structure represented by the following formula (1).
[4]前記の水溶性有機高分子が、メチルセルロース、エチルセルロース、ヒドロキシエチルセルロース、ヒドロキシプロピルセルロース、カルボキシメチルセルロース、デンプン、ウレタン変性ポリエーテル、キサンタンガム、ポリビニルアルコールからなる群より選ばれる少なくとも1種の高分子であることを特徴とする、[1]〜[3]のいずれか1項に記載の抗ウイルス剤組成物。
[5]ポリウレタン樹脂中のカルボキシル基及び/又はカルボキシレート基の含有量が0.5〜4.0質量%であることを特徴とする[1]〜[4]のいずれか1項に記載の抗ウイルス剤組成物。
[6]布帛基材の表面に、抗ウイルス性を有する層が設けられており、当該層が、メトキシシラン系第4級アンモニウム塩を含む抗ウイルス剤と、カルボキシル基及び/又はカルボキシレート基を有する水系ポリウレタン樹脂バインダーとを含む層であることを特徴とする抗ウイルス性布帛。
[7]ポリウレタンからなるシートの表面に、抗ウイルス性を有する層が設けられており、当該層が、メトキシシラン系第4級アンモニウム塩を含む抗ウイルス剤と、カルボキシル基及び/又はカルボキシレート基を有する水系ポリウレタン樹脂バインダーとを含む層であることを特徴とする抗ウイルス性ポリウレタンシート。
[8]ポリ塩化ビニルからなるシートの表面に、抗ウイルス性を有する層が設けられており、当該層が、メトキシシラン系第4級アンモニウム塩を含む抗ウイルス剤と、カルボキシル基及び/又はカルボキシレート基を有する水系ポリウレタン樹脂バインダーとを含む層であることを特徴とする抗ウイルス性ポリ塩化ビニルシート。
[4] The water-soluble organic polymer is at least one polymer selected from the group consisting of methyl cellulose, ethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, carboxymethyl cellulose, starch, urethane-modified polyether, xanthan gum, and polyvinyl alcohol. The antiviral agent composition according to any one of [1] to [3].
[5] The item according to any one of [1] to [4], wherein the content of the carboxyl group and / or the carboxylate group in the polyurethane resin is 0.5 to 4.0% by mass. Antiviral agent composition.
[6] A layer having antiviral properties is provided on the surface of the fabric base material, and the layer contains an antiviral agent containing a methoxysilane quaternary ammonium salt and a carboxyl group and / or a carboxylate group. An antiviral fabric characterized by being a layer containing a water-based polyurethane resin binder having.
[7] A layer having antiviral properties is provided on the surface of a sheet made of polyurethane, and the layer is an antiviral agent containing a methoxysilane quaternary ammonium salt and a carboxyl group and / or a carboxylate group. An antiviral polyurethane sheet, which is a layer containing a water-based polyurethane resin binder having the above.
[8] A layer having antiviral properties is provided on the surface of a sheet made of polyvinyl chloride, and the layer is an antiviral agent containing a methoxysilane quaternary ammonium salt, a carboxyl group and / or carboxy. An antiviral polyvinyl chloride sheet, which is a layer containing an aqueous polyurethane resin binder having a rate group.
本発明の抗ウイルス剤組成物は、メトキシシラン系第4級アンモニウム塩を含む抗ウイルス剤とバインダーと水溶性有機高分子とを含むものであり、抗ウイルス剤とバインダーとを含む従来の組成物より相溶性が良好であり、表面にヒドロキシル基を持たない合成繊維等に対しても、一度の加工で抗ウイルス剤を付与することができる。つまり、抗ウイルス剤処理に先立つ前処理の工程が不要となり、特別な設備を用いることなく低コストで安定的かつ効率的に、抗ウイルス性を有する布帛を製造することができ、生産効率及びコスト面で有利である。また、本発明の組成物は、水等に希釈して処理液を調製し、布帛への加工を行う際にも樹脂カス等を発生することが無く、安定性に優れる。
さらに、本発明の抗ウイルス剤組成物を用いて抗ウイルス性を有する層が表面に形成された布帛や合成皮革シート(ポリウレタンシート、ポリ塩化ビニルシート)は、洗濯耐久性の点でも優れており、長期間に渡って抗ウイルス効果を維持することができる。
The antiviral agent composition of the present invention contains an antiviral agent containing a methoxysilane quaternary ammonium salt, a binder, and a water-soluble organic polymer, and is a conventional composition containing an antiviral agent and a binder. An antiviral agent can be applied to synthetic fibers and the like, which have better compatibility and do not have a hydroxyl group on the surface, in a single process. That is, the pretreatment step prior to the antiviral treatment is not required, and the fabric having antiviral properties can be produced stably and efficiently at low cost without using special equipment, and the production efficiency and cost can be increased. It is advantageous in terms of. Further, the composition of the present invention is excellent in stability because it does not generate resin residue or the like even when a treatment liquid is prepared by diluting it with water or the like and processed into a cloth.
Furthermore, fabrics and synthetic leather sheets (polyurethane sheets, polyvinyl chloride sheets) on which an antiviral layer is formed on the surface using the antiviral agent composition of the present invention are also excellent in washing durability. , The antiviral effect can be maintained for a long period of time.
〔抗ウイルス剤〕
本発明の抗ウイルス剤組成物に含まれる抗ウイルス剤は、メトキシシラン系第4級アンモニウム塩を含む抗ウイルス剤であり、メトキシシラン系第4級アンモニウム塩は、抗ウイルス性を発現する比較的長鎖のアルキル基を有するアンモニウム基と、布帛表面のバインダーと共有結合を形成し得るアルコキシシリル基とを有している。メトキシシラン系第4級アンモニウム塩として具体的には、下記一般式(2)で表される化合物がある。
[Antiviral agent]
The antiviral agent contained in the antiviral agent composition of the present invention is an antiviral agent containing a methoxysilane quaternary ammonium salt, and the methoxysilane quaternary ammonium salt exhibits relatively antiviral properties. It has an ammonium group having a long-chain alkyl group and an alkoxysilyl group capable of forming a covalent bond with a binder on the surface of the fabric. Specific examples of the methoxysilane quaternary ammonium salt include compounds represented by the following general formula (2).
式(2)中のXとしては、塩素イオン、臭素イオンなどのハロゲンイオン、メチルカルボニルオキシイオン(アセテートイオン)、エチルカルボニルオキシイオン(プロピオネートイオン)、フェニルカルボニルオキシイオン(ベンゾエートイオン)などの有機カルボニルオキシイオン(有機カルボン酸イオン)を例示することができる。 Examples of X in the formula (2) include halogen ions such as chloride ion and bromine ion, methylcarbonyloxy ion (acetate ion), ethylcarbonyloxy ion (propionate ion), and phenylcarbonyloxy ion (benzoate ion). An organic carbonyloxy ion (organic carboxylic acid ion) can be exemplified.
式(2)中のR1の炭素原子数12〜24のアルキル基としては、ドデシル基、トリデシル基、テトラデシル基、ペンタデシル基、ヘキサデシル基、ヘプタデシル基、オクタデシル基、ノナデシル基、エイコシル基、ウンエイコシル基、ドエイコシル基、トリエイコシル基、テトラエイコシル基などが例示できる。 Examples of the alkyl group having a carbon number of 12 to 24 of R 1 in the formula (2), a dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, eicosyl group, uneicosyl group , Doeikosyl group, tridecylic acid group, tetraeikosyl group and the like can be exemplified.
式(2)中のR2及びR3の同一又は異なっていてもよい炭素原子数1〜6の低級アルキル基としては、たとえば、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、ペンチル基、へキシル基、シクロヘキシル基などを例示することができる。 Examples of the lower alkyl group having 1 to 6 carbon atoms of R 2 and R 3 in the formula (2) which may be the same or different include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group and a pentyl group. Examples include groups, hexyl groups, cyclohexyl groups and the like.
上記一般式(2)で表されるメトキシシラン系第4級アンモニウム塩の具体例としては、オクタデシルジメチル(3−トリメトキシシリルプロピル)アンモニウムクロライド、ドデシルジメチル(3−トリメトキシシリルプロピル)アンモニウムクロライド、ドデシルジイソプロピル(3−トリメトキシシリルプロピル)アンモニウムクロライド、テトラデシルジメチル(3−トリメトキシシリルプロピル)アンモニウムクロライド、テトラデシルジエチル(3−トリメトキシシシリルプロピル)アンモニウムクロライド、テトラデシルジ−n−プロピル(3−トリメトキシシリルプロピル)アンモニウムクロライド、ペンタデシルジメチル(3−トリメトキシシリルプロピル)アンモニウムクロライド、ペンタデシルジエチル(3−トリメトキシシリルプロピル)アンモニウムクロライド、ペンタデシルジ−n−プロピル(3−トリメトキシシリルプロピル)アンモニウムクロライド、ヘキサデシルジメチル(3−トリメトキシシリルプロピル)アンモニウムクロライド、ヘキサデシルジエチル(3−トリメトキシシリルプロピル)アンモニウムクロライド、ヘキサデシルジ−n−プロピル(3−トリメトキシシリルプロピル)アンモニウムクロライド、オクタデシルジエチル(3−トリメトキシシリルプロピル)アンモニウムクロライド、オクタデシルジ−n−プロピル(3−トリメトキシシリルプロピル)アンモニウムクロライド等が挙げられ、これらの中でも、より抗ウイルス性の観点からオクタデシルジメチル(3−トリメトキシシリルプロピル)アンモニウムクロライド(下記化学式(1))が好ましい。 Specific examples of the methoxysilane-based quaternary ammonium salt represented by the above general formula (2) include octadecyldimethyl (3-trimethoxysilylpropyl) ammonium chloride, dodecyldimethyl (3-trimethoxysilylpropyl) ammonium chloride, and the like. Dodecyldiisopropyl (3-trimethoxysilylpropyl) ammonium chloride, tetradecyldimethyl (3-trimethoxysilylpropyl) ammonium chloride, tetradecyldiethyl (3-trimethoxycysilylpropyl) ammonium chloride, tetradecyldi-n-propyl (3-) Trimethoxysilylpropyl) ammonium chloride, pentadecyldimethyl (3-trimethoxysilylpropyl) ammonium chloride, pentadecyldiethyl (3-trimethoxysilylpropyl) ammonium chloride, pentadecyldi-n-propyl (3-trimethoxysilylpropyl) ammonium Chloride, hexadecyldimethyl (3-trimethoxysilylpropyl) ammonium chloride, hexadecyldiethyl (3-trimethoxysilylpropyl) ammonium chloride, hexadecyldi-n-propyl (3-trimethoxysilylpropyl) ammonium chloride, octadecyldiethyl (3) -Trimethoxysilylpropyl) ammonium chloride, octadecyldi-n-propyl (3-trimethoxysilylpropyl) ammonium chloride and the like can be mentioned, and among these, octadecyldimethyl (3-trimethoxysilylpropyl) from the viewpoint of more antiviral properties. ) Ammonium chloride (the following chemical formula (1)) is preferable.
本発明の抗ウイルス剤組成物に含まれる抗ウイルス剤は、上記のメトキシシラン系第4級アンモニウム塩の1種又は2種以上であってもよいし、さらに他の抗ウイルス剤と併用することもできる。上記のメトキシシラン系第4級アンモニウム塩は、グラム陽性菌、グラム陰性菌に対する抗菌(制菌)効果、及び、インフルエンザウイルス、はしかウイルス等のエンベロープウイルスに対しても抗ウイルス作用を有している(以後、抗菌効果及び抗ウイルス効果をまとめて、抗ウイルス効果ということがある。)。さらに、抗ウイルス効果以外にも、制電効果、防臭効果も同時に有するものと考えられている。 The antiviral agent contained in the antiviral agent composition of the present invention may be one or more of the above-mentioned methoxysilane quaternary ammonium salts, or may be used in combination with other antiviral agents. You can also. The above methoxysilane quaternary ammonium salt has an antibacterial (antibacterial) effect against gram-positive and gram-negative bacteria, and an antiviral effect against enveloped viruses such as influenza virus and sardine virus. (Hereinafter, the antibacterial effect and the antiviral effect may be collectively referred to as the antiviral effect). Furthermore, in addition to the antiviral effect, it is considered to have an antistatic effect and a deodorant effect at the same time.
上記の抗ウイルス剤の濃度は、組成物中に安定に維持され、本発明の効果が得られる限り特に制限されないが、例えば、本発明の抗ウイルス剤組成物中、水等を用いて希釈を行う前の未希釈の状態で0.01〜50重量%含まれるものとでき、0.02〜20重量%含まれていればより好ましい。また、布帛に処理を行う時の処理液中の抗ウイルス剤濃度は0.01〜1.5重量%であることが好ましく、0.02〜0.45重量%であることがより好ましい。 The concentration of the above-mentioned antiviral agent is not particularly limited as long as it is stably maintained in the composition and the effect of the present invention is obtained, but for example, it is diluted with water or the like in the antiviral agent composition of the present invention. It can be contained in an undiluted state of 0.01 to 50% by weight, more preferably 0.02 to 20% by weight. Further, the concentration of the antiviral agent in the treatment liquid when the fabric is treated is preferably 0.01 to 1.5% by weight, more preferably 0.02 to 0.45% by weight.
〔水系ポリウレタン樹脂〕
本発明の抗ウイルス剤組成物におけるバインダー(水系ポリウレタン樹脂)は、ポリイソシアネート化合物、ポリオール化合物、カルボキシル基及び/又はカルボキシレート基を有するジオール化合物を反応して得られるイソシアネート基末端プレポリマーの中和物を、水中に乳化分散させたのち、アミン系鎖伸長剤を用いて水中で鎖伸長反応して得られる。これ以降、分散又は乳化することを乳化分散と表記する。
水系ポリウレタン樹脂に関して「水系」とは、そのポリウレタン樹脂の水中濃度が40質量%である乳化分散液(溶媒:水)を調製した後に該乳化分散液を20℃で12時間静置しても分離や沈降が観察されないような状態とすることが可能であることを意味する。
[Water-based polyurethane resin]
The binder (aqueous polyurethane resin) in the antiviral agent composition of the present invention is a neutralization of an isocyanate group-terminated prepolymer obtained by reacting a polyisocyanate compound, a polyol compound, a diol compound having a carboxyl group and / or a carboxylate group. The compound is emulsified and dispersed in water, and then subjected to a chain extension reaction in water using an amine-based chain extender. Hereinafter, dispersion or emulsification is referred to as emulsification dispersion.
Regarding the water-based polyurethane resin, "water-based" means that the emulsion dispersion liquid (solvent: water) having a concentration of 40% by mass in water of the polyurethane resin is prepared and then separated even if the emulsion dispersion liquid is allowed to stand at 20 ° C. for 12 hours. It means that it is possible to make it so that no sedimentation is observed.
(ポリイソシアネート化合物)
本発明に用いるポリイソシアネート化合物に特に制限はなく、例えば、芳香族ポリイソシアネート化合物、脂肪族ポリイソシアネート化合物、脂環式ポリイソシアネート化合物などを挙げることができる。芳香族ポリイソシアネート化合物としては、例えば、トルエンジイソシアネート(TDI)、キシリレンジイソシアネート(XDI)、ジフェニルメタンジイソシアネート(MDI)、ナフタレンジイソシアネート(NDI)、テトラメチルキシリレンジイソシアネートなどを挙げることができる。脂肪族ポリイソシアネート化合物としては、例えば、ヘキサメチレンジイソシアネート(HDI)などを挙げることができる。脂環式ポリイソシアネート化合物としては、例えば、1,3−ビス(イソシアナトメチル)シクロヘキサン、イソホロンジイソシアネート(IPDI)、ジシクロへキシルメタンジイソシアネート(H12MDI)、ノルボルナンジイソシアネートなどを挙げることができる。これらのポリイソシアネート化合物は、1種を単独で、又は、2種以上を組み合わせて用いることもできる。このようなポリイソシアネートの中でも、脂肪族ポリイソシアネート及び脂環式ポリイソシアネート化合物は、無黄変性を布帛やポリ塩化ビニルシート、ポリウレタンシートに与えるので好適に用いることができ、特にヘキサメチレンジイソシアネート、イソホロンジイソシアネート、ジシクロヘキシルメタンジイソシアネート、ノルボルナンジイソシアネート及び、1,3−ビス(イソシアナトメチル)シクロヘキサンを好適に用いることができる。
(Polyisocyanate compound)
The polyisocyanate compound used in the present invention is not particularly limited, and examples thereof include aromatic polyisocyanate compounds, aliphatic polyisocyanate compounds, and alicyclic polyisocyanate compounds. Examples of the aromatic polyisocyanate compound include toluene diisocyanate (TDI), xylylene diisocyanate (XDI), diphenylmethane diisocyanate (MDI), naphthalene diisocyanate (NDI), and tetramethylxylylene diisocyanate. Examples of the aliphatic polyisocyanate compound include hexamethylene diisocyanate (HDI). Examples of the alicyclic polyisocyanate compound include 1,3-bis (isocyanatomethyl) cyclohexane, isophorone diisocyanate (IPDI), dicyclohexylmethane diisocyanate (H12MDI), norbornane diisocyanate and the like. These polyisocyanate compounds may be used alone or in combination of two or more. Among such polyisocyanates, aliphatic polyisocyanates and alicyclic polyisocyanate compounds can be suitably used because they impart non-yellowing to fabrics, polyvinyl chloride sheets, and polyurethane sheets, and are particularly hexamethylene diisocyanate and isophorone. Diisocyanate, dicyclohexylmethane diisocyanate, norbornane diisocyanate, and 1,3-bis (isocyanatomethyl) cyclohexane can be preferably used.
(ポリオール化合物)
また、ポリオール化合物としては、 ポリエーテルポリオールやポリエステルポリオール、ポリカーボネートポリオールなどを挙げることができる。これらのポリオール化合物は、1種を単独で、又は、2種以上を組み合わせて用いることもできる。布帛やポリ塩化ビニルシート、ポリウレタンシートの耐摩耗性が良好となることからポリカーボネートポリオールを用いることが望ましい。
また、ポリオール化合物は数平均分子量1,000〜3,000であることが好ましい。数平均分子量がその範囲であると布帛やポリ塩化ビニルシート、ポリウレタンシートの外観品位と耐摩耗性とが良好となる。
(Polyol compound)
Moreover, as a polyol compound, a polyether polyol, a polyester polyol, a polycarbonate polyol and the like can be mentioned. These polyol compounds may be used alone or in combination of two or more. It is desirable to use a polycarbonate polyol because the abrasion resistance of the fabric, the polyvinyl chloride sheet, and the polyurethane sheet is good.
The polyol compound preferably has a number average molecular weight of 1,000 to 3,000. When the number average molecular weight is within that range, the appearance quality and abrasion resistance of the fabric, the polyvinyl chloride sheet, and the polyurethane sheet are good.
ポリエーテルポリオールとしては、例えば、エチレンオキサイド、プロピレンオキサイド及びテトラメチレンオキサイドなどの炭素数2〜4のアルキレンオキサイドの単独付加重合物又は共付加重合物(ブロック共重合でも、ランダム共重合でもかまわない)であるポリオールなどを挙げることができる。 Examples of the polyether polyol include homoaddition polymers or copolymers of alkylene oxides having 2 to 4 carbon atoms such as ethylene oxide, propylene oxide and tetramethylene oxide (block copolymerization or random copolymerization may be used). Can be mentioned, such as a polyol.
ポリカーボネートポリオールとしては、例えば、エチレングリコール、1,2−プロパンジオール、1,3−プロパンジオール、1,2−ブタンジオール、1,3−ブタンジオール、1,4−ブタンジオール、1,5−ペンタンジオール、1,6−ヘキサンジオール、3−メチル−1,5−ペンタンジオール、ネオペンチルグリコール、1,8−オクタンジオール、1,9−ノナンジオール、ジエチレングリコール、ジプロピレングリコール、1,4−シクロヘキサンジメタノール、あるいはビスフェノールAのエチレンオキサイド又はプロピレンオキサイド付加物等から選ばれる1種または2種以上のポリオール類;と、ジエチルカーボネート、ジメチルカーボネート、ジフェニルカーボネート等から選ばれる1種または2種以上のカーボネート類との脱アルコール反応、脱フェノール反応等で得られるものが挙げられる。上記ポリカーボネートポリオールは、1種を単独で用いることができ、または2種以上を組み合わせて用いることができる。 Examples of the polycarbonate polyol include ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, and 1,5-pentane. Diol, 1,6-hexanediol, 3-methyl-1,5-pentanediol, neopentyl glycol, 1,8-octanediol, 1,9-nonanediol, diethylene glycol, dipropylene glycol, 1,4-cyclohexanedi One or more polyols selected from ethylene oxide or propylene oxide adduct of methanol or bisphenol A; and one or more carbonates selected from diethyl carbonate, dimethyl carbonate, diphenyl carbonate and the like. Examples thereof are those obtained by a dealcoholization reaction with and a dephenolization reaction. The above-mentioned polycarbonate polyol may be used alone or in combination of two or more.
ポリエステルポリオールとしては、例えば、フタル酸、イソフタル酸、テレフタル酸、ナフタレンジカルボン酸、コハク酸、マロン酸、アジピン酸、セバシン酸、1,4−シクロヘキシルジカルボン酸、マレイン酸、フマル酸等から選ばれる1種または2種以上の二塩基酸と、前述のポリカーボネートポリオールの合成に用いられる1種または2種以上のポリオール類との重縮合反応により得られるものが挙げられる。上記ポリエステルポリオールは、1種を単独で用いることができ、または2種以上を組み合わせて用いることができる。 The polyester polyol is selected from, for example, phthalic acid, isophthalic acid, terephthalic acid, naphthalenedicarboxylic acid, succinic acid, malonic acid, adipic acid, sebacic acid, 1,4-cyclohexyldicarboxylic acid, maleic acid, fumaric acid and the like1 Examples thereof include those obtained by a polycondensation reaction between a seed or two or more kinds of dibasic acids and one kind or two or more kinds of polyols used in the synthesis of the above-mentioned polycarbonate polyol. The polyester polyol may be used alone or in combination of two or more.
カルボキシル基及び/又はカルボキシレート基を有するジオール化合物としては、例えば、2,2−ジメチロールプロピオン酸、2,2−ジメチロールブタン酸、及びこれらの塩を挙げることができる。さらに、このようなジオール化合物として、カルボキシル基を有するジオール化合物と、芳香族ジカルボン酸、脂肪族ジカルボン酸等とを反応させて得られるペンダント型カルボキシル基を有するポリエステルポリオールを用いることもできる。なお、前記カルボキシル基を有するジオール化合物に、ジオール成分としてカルボキシル基を有さないジオール化合物を混合して反応させても良い。これらのジオール化合物は、1種を単独で用いることができ、あるいは、2種以上を組み合わせて用いることもできる。 Examples of the diol compound having a carboxyl group and / or a carboxylate group include 2,2-dimethylolpropionic acid, 2,2-dimethylolbutanoic acid, and salts thereof. Further, as such a diol compound, a polyester polyol having a pendant type carboxyl group obtained by reacting a diol compound having a carboxyl group with an aromatic dicarboxylic acid, an aliphatic dicarboxylic acid or the like can also be used. The diol compound having a carboxyl group may be mixed with a diol compound having no carboxyl group as a diol component and reacted. One of these diol compounds can be used alone, or two or more of these diol compounds can be used in combination.
また、本発明において水系ポリウレタン樹脂中のカルボキシル基の含有量は、抗ウイルス剤の固着性または抗ウイルス剤との相溶性の観点から、水系ポリウレタン樹脂中のカルボキシル基及び/又はカルボキシレート基の含有量は、0.5質量%〜4.0質量%の範囲が好ましい。なお、カルボキシル基及び/又はカルボキシレート基の含有量は、ポリウレタン樹脂100gあたりのCOO量を原料仕込み量から計算することで求めることができる。カルボキシル基の含有量が4.0質量%を超えた場合、布帛やポリ塩化ビニルシート、ポリウレタンシートの風合いが硬くなる、屈曲時に白化が生じやすくなるなどの恐れがある。また0.5質量%以下の場合は水系ポリウレタン樹脂の貯蔵安定性が低下するため安定的な加工ができない恐れがある。 Further, in the present invention, the content of the carboxyl group in the water-based polyurethane resin is the content of the carboxyl group and / or the carboxylate group in the water-based polyurethane resin from the viewpoint of the adhesiveness of the antiviral agent or the compatibility with the antiviral agent. The amount is preferably in the range of 0.5% by mass to 4.0% by mass. The content of the carboxyl group and / or the carboxylate group can be obtained by calculating the amount of COO per 100 g of the polyurethane resin from the amount of the raw material charged. If the content of the carboxyl group exceeds 4.0% by mass, the texture of the fabric, the polyvinyl chloride sheet, and the polyurethane sheet may become hard, and whitening may easily occur during bending. If it is 0.5% by mass or less, the storage stability of the water-based polyurethane resin is lowered, so that stable processing may not be possible.
本発明においては、イソシアネート基末端プレポリマーを調製する際に、ポリオール化合物として、例えば、エチレングリコール、1,4−ブタンジオール、ヘキサメチレングリコールなどの低分子量多価アルコールを用いることもできる。
(鎖伸長剤)
鎖伸長剤としては、エチレンジアミン、プロピレンジアミン、テトラメチレンジアミン、ヘキサメチレンジアミン、ヒドラジン、4,4'−ジアミノジシクロへキシルメタン、ピペラジン、2−メチルピペラジン、イソホロンジアミン、ノルボランジアミン、ジアミノジフェニルメタン、トリレンジアミン、キシリレンジアミン、ジエチレントリアミン、トリエチレンテトラミン、トリエチレンテトラミン、テトラエチレンペンタミン、イミノビスプロピルアミンなどの低分子量ポリアミン(1級アミノ基及び2級アミノ基からなる群から選択される少なくとも1種のアミノ基を1分子中に2個以上含有するポリアミン化合物)などを挙げることができる。これらの鎖伸長剤は、1種を単独で用いることができ、あるいは、2種以上を組み合わせて用いることもできる。
In the present invention, when preparing the isocyanate group-terminated prepolymer, low molecular weight polyhydric alcohols such as ethylene glycol, 1,4-butanediol and hexamethylene glycol can also be used as the polyol compound.
(Chain extender)
Chain extenders include ethylenediamine, propylenediamine, tetramethylenediamine, hexamethylenediamine, hydrazine, 4,4'-diaminodicyclohexylmethane, piperazine, 2-methylpiperazin, isophoronediamine, norborandiamine, diaminodiphenylmethane, and tri. At least one selected from the group consisting of low molecular weight polyamines (primary amino groups and secondary amino groups) such as rangeamines, xylylenediamines, diethylenetriamines, triethylenetetramines, triethylenetetramines, tetraethylenepentamines, iminobispropylamines. A polyamine compound containing two or more seed amino groups in one molecule) and the like can be mentioned. These chain extenders may be used alone or in combination of two or more.
尚、本発明の抗ウイルス剤組成物に含有される水系ポリウレタン樹脂は、例えば、特開2006−206839号公報に開示されたリン系化合物を難燃成分として含む難燃剤ブレンドウレタン系樹脂であってもよい。 The water-based polyurethane resin contained in the antiviral agent composition of the present invention is, for example, a flame retardant-blended urethane resin containing a phosphorus-based compound disclosed in JP-A-2006-206839 as a flame-retardant component. May be good.
次に、上記水系ポリウレタン樹脂の製造方法について説明する。
(イソシアネート基末端プレポリマー)
本発明において、イソシアネート基末端プレポリマーを製造する具体的な方法としては特に制限はなく、例えば、従来公知の一段式のいわゆるワンショット法、多段式のイソシアネート重付加反応法等により製造することができる。この時の反応温度は、40〜150℃であることが好ましい。また、反応中又は反応終了後に、イソシアネート基と反応しない有機溶剤を添加することができる。このような有機溶剤としては、例えば、アセトン、メチルエチルケトン、トルエン、テトラヒドロフラン等を使用することができる。反応中には、必要に応じて、ジブチル錫ジラウレート、スタナスオクトエート、ジブチル錫ジ−2−エチルヘキソエート、トリエチルアミン、トリエチレンジアミン、N−メチルモルホリン、ビスマストリス(2−エチルヘキサノエート)等の反応触媒、あるいは燐酸、燐酸水素ナトリウム、パラトルエンスルホン酸、アジピン酸、塩化ベンゾイル等の反応抑制剤を添加してもよい。
イソシアネート基末端プレポリマーにおける残存イソシアネート基の含有率は、0.2〜4.5質量%であることが好ましい。この範囲であると、その後ポリアミンにより鎖伸張して得られる水系ポリウレタン樹脂組成物の成膜性が良好となり、また、形成されるフィルムが柔らかくなり適度な柔軟性を示す。
残存イソシアネート基含有率は以下の方法で求めることができる。
得られたウレタンプレポリマー0.3gを三角フラスコに採取し、0.1N ジブチルアミントルエン溶液10mlを配合し、溶解させた。次いで、ブロモフェノールブルー液を数滴加え、0.1N塩酸メタノール溶液で滴定し、下記式により遊離イソシアネート基含有量NCO%を求めた。
NCO%=(a−b)×0.42×f/x
a:0.1N ジブチルアミントルエン溶液10mlのみを滴定した場合の0.1N塩酸メタノール液の滴定量。
b:反応中の組成物を滴定した場合の0.1N塩酸メタノール液の滴定量。
f:0.1N 塩酸メタノール液のファクター。
x:サンプリング量。
残存イソシアネート基の含有率を上記範囲とするには、プレポリマー製造時の、原料のイソシアネート基/ヒドロキシル基のモル比を100/80〜100/60に調整することが好ましい。イソシアネート基/ヒドロキシル基のモル比が100/80未満の場合イソシアネート基末端プレポリマーの粘度が高く、乳化分散が困難になる恐れがあり、また、イソシアネート基/ヒドロキシル基のモル比が100/60を超えると、布帛やポリ塩化ビニルシート、ポリウレタンシートの風合いが硬くなる、屈曲時に白化が生じやすくなるなどの恐れがある。
Next, a method for producing the water-based polyurethane resin will be described.
(Isocyanate group-terminated prepolymer)
In the present invention, the specific method for producing the isocyanate group-terminated prepolymer is not particularly limited, and for example, it can be produced by a conventionally known one-stage so-called one-shot method, multi-stage isocyanate heavy addition reaction method, or the like. it can. The reaction temperature at this time is preferably 40 to 150 ° C. In addition, an organic solvent that does not react with the isocyanate group can be added during or after the reaction. As such an organic solvent, for example, acetone, methyl ethyl ketone, toluene, tetrahydrofuran and the like can be used. During the reaction, if necessary, dibutyltin dilaurate, stanas octoate, dibutyltin di-2-ethylhexoate, triethylamine, triethylenediamine, N-methylmorpholine, bismastris (2-ethylhexanoate) Or other reaction catalysts such as phosphoric acid, sodium hydrogen phosphate, paratoluenesulfonic acid, adipic acid, benzoyl chloride and the like may be added.
The content of the residual isocyanate group in the isocyanate group-terminated prepolymer is preferably 0.2 to 4.5% by mass. Within this range, the film-forming property of the water-based polyurethane resin composition obtained by chain extension with polyamine thereafter becomes good, and the formed film becomes soft and exhibits appropriate flexibility.
The residual isocyanate group content can be determined by the following method.
0.3 g of the obtained urethane prepolymer was collected in an Erlenmeyer flask, and 10 ml of a 0.1 N dibutylamine toluene solution was added and dissolved. Then, several drops of bromophenol blue solution were added, and the mixture was titrated with a 0.1N hydrochloric acid-methanol solution to determine the free isocyanate group content NCO% by the following formula.
NCO% = (ab) x 0.42 x f / x
a: Titration of 0.1N hydrochloric acid-methanol solution when only 10 ml of 0.1N dibutylamine toluene solution is titrated.
b: Titration of 0.1N hydrochloric acid-methanol solution when the composition under reaction is titrated.
f: Factor of 0.1N methanol hydrochloric acid solution.
x: Sampling amount.
In order to keep the residual isocyanate group content in the above range, it is preferable to adjust the molar ratio of isocyanate groups / hydroxyl groups of the raw material to 100/80 to 100/60 during the production of the prepolymer. When the molar ratio of isocyanate group / hydroxyl group is less than 100/80, the viscosity of the isocyanate group-terminated prepolymer may be high, which may make emulsion dispersion difficult, and the molar ratio of isocyanate group / hydroxyl group should be 100/60. If it exceeds the limit, the texture of the fabric, the polyvinyl chloride sheet, and the polyurethane sheet may become hard, and whitening may easily occur at the time of bending.
(中和)
イソシアネート基末端プレポリマーのカルボキシル基の中和は、イソシアネート基末端プレポリマーの調製前、調製中又は調製後に適宜公知の方法を用いて行うことができる。このようなカルボキシル基を有するイソシアネート基末端プレポリマーの中和に用いる化合物には特に制限はなく、例えば、トリメチルアミン、トリエチルアミン、トリ−n−プロピルアミン、トリブチルアミン、N−メチル−ジエタノールアミン、N,N−ジメチルモノエタノールアミン、N,N−ジエチルモノエタノールアミン、トリエタノールアミン等のアミン類、水酸化カリウム、水酸化ナトリウム、アンモニア等を挙げることができる。このような前記化合物の中でも、トリメチルアミン、トリエチルアミン、トリ−n−プロピルアミン、トリブチルアミン等の第3級アミン類が特に好ましい。
(Neutralization)
Neutralization of the carboxyl group of the isocyanate group-terminated prepolymer can be carried out by an appropriately known method before, during or after the preparation of the isocyanate group-terminated prepolymer. The compound used for neutralizing the isocyanate group-terminated prepolymer having such a carboxyl group is not particularly limited, and is, for example, trimethylamine, triethylamine, tri-n-propylamine, tributylamine, N-methyl-diethanolamine, N, N. Examples thereof include amines such as -dimethylmonoethanolamine, N, N-diethylmonoethanolamine, triethanolamine, potassium hydroxide, sodium hydroxide, ammonia and the like. Among such compounds, tertiary amines such as trimethylamine, triethylamine, tri-n-propylamine and tributylamine are particularly preferable.
(乳化分散)
本発明において、イソシアネート基末端プレポリマーの中和物を水に乳化分散させる際に用いる乳化分散機器に特に制限はなく、例えば、ホモミキサー、ホモジナイザー、ディスパー等を挙げることができる。また、イソシアネート基末端プレポリマーの中和物を水に乳化分散させる際には、イソシアネート基末端プレポリマーの中和物を、0〜40℃の温度範囲で水に乳化分散させて、イソシアネート基と水との反応を極力抑えることが好ましい。さらに、このように乳化分散させる際には、必要に応じて、燐酸、燐酸二水素ナトリウム、燐酸水素二ナトリウム、パラトルエンスルホン酸、アジピン酸、塩化ベンゾイル等の反応抑制剤を添加することができる。
(Emulsification dispersion)
In the present invention, the emulsification / dispersion device used for emulsifying and dispersing the neutralized product of the isocyanate group-terminated prepolymer in water is not particularly limited, and examples thereof include a homomixer, a homogenizer, and a disper. When the neutralized product of the isocyanate group-terminated prepolymer is emulsified and dispersed in water, the neutralized product of the isocyanate group-terminated prepolymer is emulsified and dispersed in water in a temperature range of 0 to 40 ° C. to form an isocyanate group. It is preferable to suppress the reaction with water as much as possible. Furthermore, when emulsifying and dispersing in this way, reaction inhibitors such as phosphoric acid, sodium dihydrogen phosphate, disodium hydrogen phosphate, p-toluenesulfonic acid, adipic acid, and benzoyl chloride can be added, if necessary. ..
(アミン伸長)
本発明においては、このように水に乳化分散させた前記イソシアネート基末端プレポリマーを、1級アミノ基及び2級アミノ基からなる群から選択される少なくとも1種のアミノ基を1分子中に2個以上含有するポリアミン化合物を用いて鎖伸長させる。
イソシアネート基末端プレポリマーとポリアミン化合物との反応は、20〜50℃の反応温度で、通常、30〜120分間で完結する。
(Amine extension)
In the present invention, the isocyanate group-terminated prepolymer thus emulsified and dispersed in water contains at least one amino group selected from the group consisting of primary amino groups and secondary amino groups in one molecule. Chain extension is carried out using a polyamine compound contained in an amount of one or more.
The reaction between the isocyanate group-terminated prepolymer and the polyamine compound is usually completed in 30 to 120 minutes at a reaction temperature of 20 to 50 ° C.
(脱溶剤)
イソシアネート基末端プレポリマーを製造する際に前述の有機溶剤を使用した場合には、例えば、鎖伸長反応又は乳化分散後に、減圧下、30〜80℃で溶媒を留去することが望ましい。このような調製方法によってポリウレタン樹脂は、ポリウレタン樹脂の乳化分散液として得ることができる。
ポリウレタン樹脂の乳化分散液中の樹脂固形分(不揮発分)濃度は、20〜60%の範囲が好ましい。樹脂固形分濃度は、水を追加または留去することで調整することも可能である。
(Solvent removal)
When the above-mentioned organic solvent is used in producing the isocyanate group-terminated prepolymer, it is desirable to distill off the solvent at 30 to 80 ° C. under reduced pressure after, for example, a chain extension reaction or emulsification dispersion. By such a preparation method, the polyurethane resin can be obtained as an emulsified dispersion of the polyurethane resin.
The resin solid content (nonvolatile content) concentration in the emulsion dispersion of the polyurethane resin is preferably in the range of 20 to 60%. The resin solid content concentration can also be adjusted by adding or distilling water.
〔アクリル系樹脂〕
本発明の抗ウイルス剤組成物では、バインダーとして上記の水系ポリウレタン樹脂に加え、アクリル系樹脂を併用することが好ましい。水系ポリウレタン樹脂とアクリル系樹脂の重量比率は適宜選択できるが、1:0.1〜1であることが好ましい。
バインダーとして含有されるアクリル系樹脂のモノマーとしては、(メタ)アクリル酸メチル、(メタ)アクリル酸エチル、(メタ)アクリル酸2−エチルヘキシル、(メタ)アクリル酸ラウリル、(メタ)アクリル酸ステアリル、(メタ)アクリル酸シクロヘキシル、(メタ)アクリル酸イソボルニル、(メタ)アクリル酸ベンジル、(メタ)アクリル酸、(メタ)アクリル酸グリシジル、(メタ)アクリル酸ジメチルアミノエチル、(メタ)アクリル酸ジエチルアミノエチル、(メタ)アクリル酸2−ヒドロキシエチル、(メタ)アクリル酸2−ヒドロキシプロピル等の(メタ)アクリル酸誘導体;スチレン、α−メチルスチレン、p−メチルスチレン等の芳香族ビニル化合物;アクリルアミド、ダイアセトンアクリルアミド、メタクリルアミド、マレイン酸アミド等のアクリルアミド類;ビニルピロリドン等の複素環式ビニル化合物;塩化ビニル、アクリロニトリル、ビニルエーテル、ビニルケトン、ビニルアミド等のビニル化合物;エチレン、プロピレン等のα−オレフィン;マレイン酸、フマル酸、イタコン酸及びそれらの誘導体等が挙げられる。ここで、(メタ)アクリル酸とは、アクリル酸又はメタクリル酸を表す。また、このようなモノマーは、1種を単独で用いることができ、又は、2種以上を組み合わせて用いることもできる。
[Acrylic resin]
In the antiviral agent composition of the present invention, it is preferable to use an acrylic resin in combination with the above-mentioned aqueous polyurethane resin as a binder. The weight ratio of the water-based polyurethane resin to the acrylic resin can be appropriately selected, but is preferably 1: 0.1 to 1.
Examples of the monomer of the acrylic resin contained as a binder include methyl (meth) acrylate, ethyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, lauryl (meth) acrylate, and stearyl (meth) acrylate. Cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, benzyl (meth) acrylate, (meth) acrylic acid, glycidyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate , (Meta) acrylic acid derivatives such as 2-hydroxyethyl (meth) acrylic acid, 2-hydroxypropyl (meth) acrylic acid; aromatic vinyl compounds such as styrene, α-methylstyrene, p-methylstyrene; acrylamide, die Acrylamides such as acetone acrylamide, methacrylamide and maleic acid amide; heterocyclic vinyl compounds such as vinylpyrrolidone; vinyl compounds such as vinyl chloride, acrylonitrile, vinyl ether, vinyl ketone and vinylamide; α-olefins such as ethylene and propylene; maleic acid , Fumaric acid, itaconic acid and derivatives thereof. Here, (meth) acrylic acid represents acrylic acid or methacrylic acid. Further, such a monomer may be used alone or in combination of two or more.
〔分散剤〕
本発明の抗ウイルス剤組成物には、上記の抗ウイルス剤とポリウレタン樹脂を同一液中に分散させるための分散剤として水溶性有機高分子が配合されており、このような水溶性有機高分子としては、メチルセルロース、エチルセルロース、ヒドロキシエチルセルロース、ヒドロキシプロピルセルロース、カルボキシメチルセルロース、デンプン、ウレタン変性ポリエーテル、キサンタンガム、ポリビニルアルコールからなる群より選ばれる少なくとも1種の高分子であることが好ましく、特にウレタン変性ポリエーテルまたはキサンタンガムが好ましい。
本発明において水溶性とは、0.1質量%の濃度で20℃の水に溶解させた場合に透明となることをさす。
ウレタン変性ポリエーテルとしては、末端に疎水基を有し、分子鎖中にウレタン結合を有するウレタン変性ポリエーテルが含有されてもよく、例えば特許第3972234号、または、特許第4528908号に記載されているウレタン変性ポリエーテル:
[Dispersant]
The antiviral agent composition of the present invention contains a water-soluble organic polymer as a dispersant for dispersing the above-mentioned antiviral agent and polyurethane resin in the same liquid, and such a water-soluble organic polymer is blended. The polymer is preferably at least one polymer selected from the group consisting of methyl cellulose, ethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, carboxymethyl cellulose, starch, urethane-modified polyether, xanthan gum, and polyvinyl alcohol, and particularly urethane-modified poly. Ether or xanthan gum is preferred.
In the present invention, water-soluble means that it becomes transparent when dissolved in water at 20 ° C. at a concentration of 0.1% by mass.
As the urethane-modified polyether, a urethane-modified polyether having a hydrophobic group at the terminal and a urethane bond in the molecular chain may be contained, and is described in, for example, Patent No. 39722334 or Patent No. 45288908. Urethane modified polyether:
R1-X-(PEG-X-R2-X)m-PEG-X-R1'
(R1,R1':炭素数8〜36のアルキル基あるいは芳香環を有する炭化水素基でR1とR1'は同一でも異なっていても良い、R2:NCO基を除く炭素数6〜36のジイソシアネート残基、X:ウレタン結合、PEG:分子量1,500〜33,000のポリエチレングリコール残基、m:0以上の整数);
R1-X- (PEG-X-R2-X) m-PEG-X-R1'
(R1, R1': an alkyl group having 8 to 36 carbon atoms or a hydrocarbon group having an aromatic ring, R1 and R1'may be the same or different, R2: a diisocyanate residue having 6 to 36 carbon atoms excluding the NCO group. Group, X: Urethane bond, PEG: Polyethylene glycol residue with molecular weight of 1,500 to 33,000, m: Integer of 0 or more);
R1-Y-R2-(X-PEG-X-R3)m-X-PEG-X-R2-Y-R1'
(R1, R1': 炭素数8〜36のアルキル基あるいは芳香環を有する炭化水素基でR1とR1'は同一でも異なっていても良い、R2,R3:NCO基を除く炭素数6〜36のジイソシアネート残基でR2とR3は同一でも異なっていても良い、X:ウレタン結合、Y:ウレタン結合あるいはウレア結合、PEG:分子量1,500〜 33,000のポリエチレングリコール残基、m:0以上の整数);
R1-Y-R2- (X-PEG-X-R3) m-X-PEG-X-R2-Y-R1'
(R1, R1': an alkyl group having 8 to 36 carbon atoms or a hydrocarbon group having an aromatic ring, R1 and R1'may be the same or different, R2, R3: 6 to 36 carbon atoms excluding the NCO group. R2 and R3 may be the same or different in the diisocyanate residue, X: urethane bond, Y: urethane bond or urea bond, PEG: polyethylene glycol residue having a molecular weight of 1,500 to 33,000, m: 0 or more. integer);
R1-(OA)p-X-R2-(X-PEG-X-R3)m-X-(AO)q-R1'
(R1,R1':炭素数8〜36のアルキル基あるいは芳香環を有する炭化水素基でR1とR1'は同一でも異なっていても良い、R2,R3:NCO基を除く炭素数6〜36のジイソシアネート残基でR2とR3は同一でも異なっていても良い、X:ウレタン結合、A:炭素数2〜4の炭化水素で少なくともエチレンを含む炭化水素残基、m:0以上の整数、p,q:1〜200の整数でpとqは同一でも異なっていても良い);
R1- (OA) p-X-R2- (X-PEG-X-R3) m-X- (AO) q-R1'
(R1, R1': an alkyl group having 8 to 36 carbon atoms or a hydrocarbon group having an aromatic ring, R1 and R1'may be the same or different, R2, R3: 6 to 36 carbon atoms excluding the NCO group. R2 and R3 may be the same or different in the diisocyanate residue, X: urethane bond, A: hydrocarbon residue having 2 to 4 carbon atoms and containing at least ethylene, m: integer of 0 or more, p, q: An integer from 1 to 200, p and q may be the same or different);
(R1,R1',R1":炭素数8〜36のアルキル基あるいは芳香環を有する炭化水素基で、R1、R1'とR1"は同一でも異なっていても良い、R4:NCO基を除く多官能ポリイソシアネート残基、A:炭素数2〜4の炭化水素で少なくともエチレンを含む炭化水素残基、X:ウレタン結合、i,j,k:0以上の整数でかつ(i+j+k)が3以上の整数、p,q,r:1〜200の整数で、p、q とrは同一でも異なっていても良い); (R1, R1', R1 ": Hydrocarbon groups having an alkyl group or an aromatic ring having 8 to 36 carbon atoms, and R1, R1'and R1" may be the same or different, R4: many excluding NCO groups. Functional polyisocyanate residue, A: hydrocarbon residue having 2 to 4 carbon atoms and containing at least ethylene, X: urethane bond, i, j, k: an integer of 0 or more and (i + j + k) of 3 or more Integer, p, q, r: an integer of 1 to 200, p, q and r may be the same or different);
(R1,R1',R1":炭素数8〜36のアルキル基あるいは芳香環を有する炭化水素基で、R1、R1'とR1"は同一でも異なっていても良い、R4:NCO基を除く多官能ポリイソシアネート残基、A:炭素数2〜4の炭化水素で少なくともエチレンを含む炭化水素残基、X:ウレタン結合、Y:ウレタン結合あるいはウレア結合、i,j,k:0以上の整数でかつ(i+j+k)が3以上の整数、p,q:1〜200の整数で、pとqは同一でも異なっていても良い); (R1, R1', R1 ": Hydrocarbon groups having an alkyl group or an aromatic ring having 8 to 36 carbon atoms, and R1, R1'and R1" may be the same or different, R4: many excluding NCO groups. Functional polyisocyanate residue, A: hydrocarbon residue having 2 to 4 carbon atoms and containing at least ethylene, X: urethane bond, Y: urethane bond or urea bond, i, j, k: 0 or more integers And (i + j + k) is an integer of 3 or more, p, q: an integer of 1 to 200, and p and q may be the same or different);
(R1,R1',R1":炭素数8〜36のアルキル基あるいは芳香環を有する炭化水素基で、R1、R1'とR1"は同一でも異なっていても良い、R5:活性水素を除く多官能ポリオールあるいはポリアミン残基、A:炭素数2〜4の炭化水素で少なくともエチレンを含む炭化水素残基、X:ウレタン結合、i,j,k:0以上の整数でかつ(i+j+k)が3以上の整数、p,q,r:1〜200の整数で、p、qとrは同一でも異なっていても良い); (R1, R1', R1 ": Hydrocarbon groups having an alkyl group or an aromatic ring having 8 to 36 carbon atoms, and R1, R1'and R1" may be the same or different. R5: Many excluding active hydrogen Functional polyol or polyamine residue, A: hydrocarbon residue having 2 to 4 carbon atoms and containing at least ethylene, X: urethane bond, i, j, k: an integer of 0 or more and (i + j + k) of 3 or more Integer, p, q, r: an integer of 1 to 200, p, q and r may be the same or different);
下記の一般式(3)で示される重量平均分子量10,000以上40,000未満の化合物Aが20質量%以上80質量%未満と、一般式(4)で示される重量平均分子量40,000以上140,000未満の化合物Bが20質量%以上80質量%未満とを必須成分として含有することを特徴とする組成物: Compound A having a weight average molecular weight of 10,000 or more and less than 40,000 represented by the following general formula (3) is 20% by mass or more and less than 80% by mass, and a weight average molecular weight represented by the general formula (4) is 40,000 or more. A composition characterized by containing 20% by mass or more and less than 80% by mass of compound B of less than 140,000 as an essential component:
(式中、X1、X2は炭素数15〜24の炭化水素基であり、Yはジイソシアネート化合物から導かれる2価の有機残基であり、OR、OR’、OR”は炭素数2〜4のオキシアルキレン基であり、a,b,dは1〜500の整数であり、cは1以上の整数である。) (In the formula, X1 and X2 are hydrocarbon groups having 15 to 24 carbon atoms, Y is a divalent organic residue derived from a diisocyanate compound, and OR, OR', OR "are carbon atoms 2 to 4. It is an oxyalkylene group, a, b, d are integers of 1 to 500, and c is an integer of 1 or more.)
(式中、X3、X4は炭素数4〜24の炭化水素基であり、Yはジイソシアネート化合物から導かれる2価の有機残基であり、OR、OR’、OR”は炭素数2〜4のオキシアルキレン基であり、a,b,dは1〜500の整数であり、cは1以上の整数。)
等が挙げられる。
(In the formula, X3 and X4 are hydrocarbon groups having 4 to 24 carbon atoms, Y is a divalent organic residue derived from a diisocyanate compound, and OR, OR', OR "are carbon atoms 2 to 4". It is an oxyalkylene group, a, b, d are integers of 1 to 500, and c is an integer of 1 or more.)
And so on.
また本発明の抗ウイルス剤組成物には、各種の添加剤等が含まれていてもよい。例えば、本発明の効果を妨げない限りにおいて、乳化剤、増粘剤、防腐剤、緩衝材、pH調整剤等が含まれていてもよい。 Further, the antiviral agent composition of the present invention may contain various additives and the like. For example, an emulsifier, a thickener, a preservative, a cushioning material, a pH adjuster and the like may be contained as long as the effects of the present invention are not impaired.
〔抗ウイルス性布帛〕
本発明はまた、前記の抗ウイルス剤組成物が処理されている布帛に関する。メトキシシラン系第4級アンモニウム塩を含む抗ウイルス剤は、従来、含酸素官能基を表面に有さない布帛には固定化されにくく、固定化を行う場合には前処理が必要とされていたが、本発明の抗ウイルス剤組成物によれば、1回の処理で、すなわち同浴で、バインダーと抗ウイルス剤とを布帛に付与することができる。また、本発明の抗ウイルス剤組成物によれば、従来の同浴処理の場合に比べ、樹脂カス等の発生が少ない。
布帛は、織物、編物、不織布のいずれであってもよく、用途及び目的によって適宜選択できる。布帛の材質は、天然繊維、化学繊維、又はこれらの組み合わせであってもよく、天然繊維としては綿、ウール、絹、麻等、化学繊維としてはポリエステル、ポリウレタン、ポリアミド、レーヨン、アクリル等が挙げられ、これらを単独、又は組み合わせた布帛を選択することができる。さらに、用途及び意匠の観点から、他の繊維、例えば、金属繊維、ガラス繊維等の無機繊維が含まれていてもよい。また、これらの布帛に対して各種の加工、例えば、難燃加工や防汚加工等がされた布帛であってもよい。例えば、自動車のシート等の車両内装用途では主にポリエステル系布帛が選択される。
[Antiviral fabric]
The present invention also relates to fabrics on which the antiviral composition is treated. Conventionally, antiviral agents containing a methoxysilane quaternary ammonium salt are difficult to be immobilized on a cloth having no oxygen-containing functional group on the surface, and pretreatment is required for immobilization. However, according to the antiviral agent composition of the present invention, the binder and the antiviral agent can be applied to the cloth in one treatment, that is, in the same bath. Further, according to the antiviral agent composition of the present invention, less resin residue and the like are generated as compared with the case of the conventional bath treatment.
The fabric may be a woven fabric, a knitted fabric, or a non-woven fabric, and can be appropriately selected depending on the intended use and purpose. The material of the fabric may be a natural fiber, a chemical fiber, or a combination thereof, and examples of the natural fiber include cotton, wool, silk, linen, etc., and examples of the chemical fiber include polyester, polyurethane, polyamide, rayon, acrylic and the like. It is possible to select a fabric in which these are used alone or in combination. Further, from the viewpoint of use and design, other fibers, for example, inorganic fibers such as metal fibers and glass fibers may be contained. Further, these fabrics may be subjected to various processing, for example, flame-retardant processing, antifouling processing, or the like. For example, polyester-based fabrics are mainly selected for vehicle interior applications such as automobile seats.
布帛のうち、例えば綿やウール等の表面にヒドロキシル基を有する繊維には、上記の抗ウイルス剤を比較的固定化しやすいが、さらに本発明の抗ウイルス剤組成物を用いると、1回の処理で、多回数の洗濯を経ても抗ウイルス剤が脱落しない洗濯耐久性にも優れた布帛を得ることができる。 Of the fabrics, for example, fibers having a hydroxyl group on the surface such as cotton and wool are relatively easy to immobilize the above antiviral agent, but further, when the antiviral agent composition of the present invention is used, one treatment is performed. Therefore, it is possible to obtain a fabric having excellent washing durability in which the antiviral agent does not fall off even after a large number of washings.
布帛に付与される抗ウイルス剤及びバインダーの付着量は、本発明の効果を有する限り特に制限されないが、例えば、抗ウイルス剤の付着量を0.01〜15g/m2とでき、0.03〜5g/m2とすることがより好ましい。抗ウイルス剤が0.03g/m2よりも少ないと十分な抗ウイルス効果を得ることが難しく、5g/m2を超えると燃焼性低下のおそれがある。また、バインダーの付着量は0.01〜15g/m2とでき、0.06〜5g/m2とすることがより好ましい。バインダーが0.06g/m2よりも少ないと抗ウイルス剤の洗濯耐久性が低下するおそれがあり、5g/m2を超えると素材の柔らかさが損なわれるおそれがある。 The amount of the antiviral agent and the binder attached to the fabric is not particularly limited as long as it has the effect of the present invention. For example, the amount of the antiviral agent attached can be 0.01 to 15 g / m 2 and 0.03. More preferably, it is ~ 5 g / m 2. If the amount of antiviral agent is less than 0.03 g / m 2, it is difficult to obtain a sufficient antiviral effect, and if it exceeds 5 g / m 2 , flammability may decrease. Further, the adhesion amount of the binder can be a 0.01~15g / m 2, and more preferably a 0.06~5g / m 2. If the amount of the binder is less than 0.06 g / m 2 , the washing durability of the antiviral agent may be lowered, and if it exceeds 5 g / m 2 , the softness of the material may be impaired.
布帛にはさらに、本発明の効果を有する限りにおいて、さらなる添加剤等が含まれていてもよい。このような添加剤等としては例えば、例えば、着色剤、酸化防止剤、光安定剤、紫外線吸収剤、難燃剤、柔軟剤や他の熱可塑性樹脂等が添加されていてもよい。 The fabric may further contain additional additives and the like as long as it has the effect of the present invention. As such additives and the like, for example, colorants, antioxidants, light stabilizers, ultraviolet absorbers, flame retardants, softeners, other thermoplastic resins and the like may be added.
〔抗ウイルス性布帛の製造方法〕
本発明の抗ウイルス剤組成物に含まれるバインダーであるカルボキシル基及び/又はカルボキシレート基を有する水系ポリウレタン樹脂は、従来公知の方法で製造することができ、例えば、固形分が10〜50重量%である水系分散体又は乳化液として入手可能である。また、本発明の組成物に含まれる抗ウイルス剤は例えば、固形分が40〜80重量%の水系分散体、水/アルコール溶液、或いは乳化液として入手可能である。これらの抗ウイルス剤とバインダーと分散剤とを、アルコール及び/又は水で、所定の濃度になるように希釈して、布帛に抗ウイルス剤を付与するための処理液として用いることができる。
[Manufacturing method of antiviral fabric]
The water-based polyurethane resin having a carboxyl group and / or a carboxylate group, which is a binder contained in the antiviral agent composition of the present invention, can be produced by a conventionally known method, for example, having a solid content of 10 to 50% by weight. It is available as an aqueous dispersion or an emulsion. Further, the antiviral agent contained in the composition of the present invention is available as, for example, an aqueous dispersion having a solid content of 40 to 80% by weight, a water / alcohol solution, or an emulsion. These antiviral agents, binders and dispersants can be diluted with alcohol and / or water to a predetermined concentration and used as a treatment liquid for imparting the antiviral agent to the fabric.
布帛に抗ウイルス剤を処理する際、処理液における抗ウイルス剤の濃度は例えば、0.01〜1.5重量%(抗ウイルス剤の有効成分濃度)とすることができ、効率及びコストの観点からは0.02〜0.45重量%とすることが好ましい。処理液は、水及び/又は有機溶媒(例えば、エタノール、プロパノール、アセトン、アセトニトリル)、又はこれらの混合物を溶媒として用いることができる。また、処理液におけるバインダーの濃度は例えば、0.005〜1重量%(バインダーの有効成分濃度)とすることができ、効率及びコストの観点からは0.01〜0.2重量%とすることが好ましい。処理液における分散剤の濃度は例えば、0.01〜10重量%(分散剤の有効成分濃度)とすることができ、効率及びコストの観点からは0.1〜5重量%とすることが好ましい。 When treating the cloth with an antiviral agent, the concentration of the antiviral agent in the treatment liquid can be, for example, 0.01 to 1.5% by weight (the concentration of the active ingredient of the antiviral agent), from the viewpoint of efficiency and cost. From 0.02 to 0.45% by weight, it is preferable. As the treatment liquid, water and / or an organic solvent (for example, ethanol, propanol, acetone, acetonitrile) or a mixture thereof can be used as the solvent. The concentration of the binder in the treatment liquid can be, for example, 0.005 to 1% by weight (the concentration of the active ingredient of the binder), and 0.01 to 0.2% by weight from the viewpoint of efficiency and cost. Is preferable. The concentration of the dispersant in the treatment liquid can be, for example, 0.01 to 10% by weight (the concentration of the active ingredient of the dispersant), and is preferably 0.1 to 5% by weight from the viewpoint of efficiency and cost. ..
いずれの場合も、まず、上述の抗ウイルス剤、バインダー及び分散剤を、所定の濃度になるように、アルコール及び/又は水で希釈して処理液を調製する。続いて、当該処理液と布帛とを接触させて、抗ウイルス性を有する布帛を製造する。 In either case, first, the above-mentioned antiviral agent, binder and dispersant are diluted with alcohol and / or water to a predetermined concentration to prepare a treatment liquid. Subsequently, the treatment liquid is brought into contact with the cloth to produce a cloth having antiviral properties.
処理液と布帛とを接触させる方法としては、例えばDip−Nip法、吸尽法、コーティング法等が挙げられる。図1に示されるようなDip−Nip法で処理を行う場合、まず、布帛を処理液に浸漬し、マングル等で絞った後に加熱乾燥し、布帛に処理液を付着させる。続いて、加熱乾燥処理を行って、抗ウイルス剤を固定化することができる。 Examples of the method for bringing the treatment liquid into contact with the fabric include a Dip-Nip method, an exhaustion method, a coating method and the like. When the treatment is performed by the Dip-Nip method as shown in FIG. 1, first, the cloth is immersed in the treatment liquid, squeezed with a mangle or the like, and then heat-dried to attach the treatment liquid to the cloth. Subsequently, a heat-drying treatment can be performed to immobilize the antiviral agent.
処理温度は特に制限されず、常温を含む温度範囲で行うことができる。例えば、110℃〜180℃において処理を行う。メトキシシラン系第4級アンモニウム塩は、比較的短時間で物品の表面に固定化されるものと考えられており、処理時間は30秒〜10分、好ましくは1分〜3分とすることができる。 The treatment temperature is not particularly limited and can be carried out in a temperature range including room temperature. For example, the treatment is performed at 110 ° C. to 180 ° C. The methoxysilane quaternary ammonium salt is considered to be immobilized on the surface of the article in a relatively short time, and the treatment time may be 30 seconds to 10 minutes, preferably 1 minute to 3 minutes. it can.
吸尽法で処理を行う場合、抗ウイルス剤とバインダーと分散剤とを含む組成物(処理液)を80℃〜140℃に加温し、続いて液中に布帛を浸漬し、マングル等で絞った後に加熱乾燥し、布帛に抗ウイルス剤を固定化することができる。 When the treatment is carried out by the exhaustion method, the composition (treatment liquid) containing the antiviral agent, the binder and the dispersant is heated to 80 ° C. to 140 ° C., and then the cloth is immersed in the liquid and used with a mangle or the like. After squeezing, it is heated and dried to immobilize the antiviral agent on the fabric.
コーティング法で処理を行う場合、本発明の抗ウイルス剤組成物を適切な粘度を有するように調整し、組成物(処理液)を布帛にコーティングした後乾燥させて、抗ウイルス剤を固定化することができる。コーティング方法としては、特に限定されるものではないが、例えばグラビアロール加工、スプレー加工、ロールコーター加工、ジェットプリント加工、転写プリント加工、スクリーンプリント加工等が挙げられる。 When the treatment is carried out by the coating method, the antiviral agent composition of the present invention is adjusted to have an appropriate viscosity, and the composition (treatment liquid) is coated on the fabric and then dried to immobilize the antiviral agent. be able to. The coating method is not particularly limited, and examples thereof include gravure roll processing, spray processing, roll coater processing, jet printing processing, transfer printing processing, screen printing processing, and the like.
バインダー、抗ウイルス剤及び分散剤を含む処理液を付与した布帛の乾燥・熱処理温度は、100〜190℃とすることができ、110〜160℃であることが好ましい。 The drying / heat treatment temperature of the fabric to which the treatment liquid containing the binder, the antiviral agent and the dispersant is applied can be 100 to 190 ° C., preferably 110 to 160 ° C.
布帛に抗ウイルス剤、バインダー及び分散剤を含む処理液を処理した後は、必要に応じて洗浄し、自然乾燥させてもよいし、加熱乾燥を行うこともできる。加熱乾燥の場合、例えば、ドライヤー、ギアオーブン、テンター等の加熱乾燥装置を使用し、乾燥することができる。また、抗ウイルス剤と布帛との接触には、他にも、噴霧や塗布によることができる。 After treating the fabric with a treatment liquid containing an antiviral agent, a binder and a dispersant, the fabric may be washed and air-dried if necessary, or may be heat-dried. In the case of heat-drying, for example, a heat-drying device such as a dryer, a gear oven, or a tenter can be used for drying. In addition, the contact between the antiviral agent and the cloth can be performed by spraying or coating.
また、乾燥・熱処理時間は、製造する布帛の材質、目付けや用途によって適宜選択することができるが、1〜5分間であることが好ましい。乾燥・熱処理には、ループ式乾燥機、ネット式ドライヤー、オーブン、ヒートセッターなどの装置を用いることができる。 The drying / heat treatment time can be appropriately selected depending on the material, basis weight and application of the fabric to be manufactured, but is preferably 1 to 5 minutes. For drying and heat treatment, devices such as a loop dryer, a net dryer, an oven, and a heat setter can be used.
〔抗ウイルス性ポリウレタンシート及びその製造方法〕
前記の抗ウイルス剤組成物を用いて製造された本発明の抗ウイルス性ポリウレタンシートは、例えば、図2(a)に示されるような層構成を有しており、(b)に示される工程によって製造される。
図2(b)に例示した工程では、最初に離型紙(凹凸柄のある紙であってもよい)の表面に表皮樹脂を塗布し、乾燥を行って表皮層を設け、次に、当該表皮層の表面にさらに接着樹脂を塗布して乾燥を行い、接着樹脂層を介して基布と貼り合わせ、ロール状に巻き取る。その後、巻き取った状態のまま1日以上養生して接着樹脂を硬化させ、離型紙を剥離してポリウレタンシートを得た後、最後に、表皮樹脂により形成された表皮層の表面に、抗ウイルス剤を含む表面処理樹脂液を塗布して乾燥を行うと、本発明の抗ウイルス性ポリウレタンシートが製造できる。
尚、本発明では、図2(a)の層構成のように、表皮層の上に表面ベース処理層として、抗ウイルス剤(メトキシシラン系第4級アンモニウム塩)を含まない組成の処理液を用いて表面処理層を設け、この層の上にさらに、抗ウイルス剤を含む組成の処理液を用いて抗ウイルス表面処理層を設けてもよい。
[Antiviral polyurethane sheet and its manufacturing method]
The antiviral polyurethane sheet of the present invention produced by using the antiviral agent composition has, for example, a layer structure as shown in FIG. 2 (a), and the step shown in (b). Manufactured by.
In the process illustrated in FIG. 2B, first, a skin resin is applied to the surface of the release paper (which may be a paper having an uneven pattern), and the surface is dried to provide a skin layer, and then the skin. An adhesive resin is further applied to the surface of the layer, dried, bonded to the base cloth via the adhesive resin layer, and wound into a roll. Then, the adhesive resin is cured by curing for one day or more in the wound state, the release paper is peeled off to obtain a polyurethane sheet, and finally, an antivirus is applied to the surface of the epidermis layer formed of the epidermis resin. The antiviral polyurethane sheet of the present invention can be produced by applying a surface treatment resin solution containing an agent and drying.
In the present invention, as shown in the layer structure of FIG. 2A, a treatment liquid having a composition that does not contain an antiviral agent (methoxysilane quaternary ammonium salt) is provided as a surface-based treatment layer on the epidermis layer. A surface treatment layer may be provided by using the above layer, and an antiviral surface treatment layer may be further provided on the layer by using a treatment liquid having a composition containing an antiviral agent.
〔抗ウイルス性ポリ塩化ビニルシート及びその製造方法〕
前記の抗ウイルス剤組成物を用いて製造された本発明の抗ウイルス性ポリ塩化ビニルシートは、例えば、図3(a)に示されるような層構成を有しており、(b)に示される工程によって製造される。
図3(b)に例示した工程では、最初に離型紙(凹凸柄のある紙であってもよい)の表面に表皮樹脂を塗布し、乾燥を行って表皮層を設け、次に、当該表皮層の表面にさらに発泡樹脂を塗布して乾燥を行い、発泡層を形成させた後、この層の表面に接着樹脂を塗布し、この接着樹脂層を介して基布と貼り合わせ、乾燥を行った後に離型紙を剥離してポリ塩化ビニル合皮を得る。最後に、表皮樹脂により形成された表皮層の表面に、抗ウイルス剤を含む表面処理樹脂液を塗布して乾燥を行うと、本発明の抗ウイルス性ポリ塩化ビニルシートが製造できる。
尚、本発明では、図3(a)の層構成のように、層間の接着性を高める目的で、表皮層の上に抗ウイルス剤(メトキシシラン系第4級アンモニウム塩)を含まずにアクリル系樹脂を含む組成を有した処理液を用いて表面ベース処理層を設け、この層の上にさらに抗ウイルス剤を含まない表面処理層/抗ウイルス表面処理層、又は、抗ウイルス剤を含む表面処理層(抗ウイルス表面処理層)を設けてもよい。
[Antiviral polyvinyl chloride sheet and its manufacturing method]
The antiviral polyvinyl chloride sheet of the present invention produced by using the antiviral agent composition has, for example, a layer structure as shown in FIG. 3 (a) and is shown in (b). Manufactured by the process of
In the process illustrated in FIG. 3 (b), first, a skin resin is applied to the surface of the release paper (which may be a paper with an uneven pattern), dried to provide a skin layer, and then the skin. A foamed resin is further applied to the surface of the layer and dried to form a foamed layer, and then an adhesive resin is applied to the surface of this layer, which is bonded to the base cloth via the adhesive resin layer and dried. After that, the release paper is peeled off to obtain a polyvinyl chloride synthetic leather. Finally, the antiviral polyvinyl chloride sheet of the present invention can be produced by applying a surface-treated resin solution containing an antiviral agent to the surface of the epidermis layer formed of the epidermis resin and drying the surface.
In the present invention, as shown in the layer structure of FIG. 3A, acrylic is not contained on the epidermis layer without an antiviral agent (methoxysilane-based quaternary ammonium salt) for the purpose of enhancing the adhesiveness between the layers. A surface-based treatment layer is provided using a treatment liquid having a composition containing a based resin, and a surface treatment layer / antiviral surface treatment layer containing no antiviral agent or a surface containing an antiviral agent is further provided on the surface-based treatment layer. A treatment layer (antiviral surface treatment layer) may be provided.
以下、本発明及び比較例に基づいて本発明をより具体的に説明するが、本発明はこれらに限定されるものではない。 Hereinafter, the present invention will be described in more detail based on the present invention and comparative examples, but the present invention is not limited thereto.
〔本発明の抗ウイルス剤組成物中に含有される水系ポリウレタン樹脂の合成例〕
(合成例1)
攪拌機、還流冷却管、温度計及び窒素吹込み管を備えた4ツ口フラスコに、1,6−ヘキサンジオールポリカーボネートポリオール(分子量1,000)251.9g、DMPA(ジメチロールプロピオン酸)10.3g、1,4−BD(ブタンジオール)3.4g、溶媒としてメチルエチルケトン 114.5gを量り取り、均一に混合した後、ポリイソシアネートとしてとしてHDI(ヘキサメチレンジイソシアネート)77.0gを加え、80±5℃で180分間反応させ、イソシアネート基の含有量が1.68質量%である末端イソシアネート基含有ウレタンプレポリマーのメチルエチルケトン溶液を得た。その後60℃でトリエチルアミン7.3gを加え中和反応を行う。次に水643.2gを徐々に加えて攪拌し、前記末端イソシアネート基含有ウレタンプレポリマーを乳化分散させた。この乳化分散液に、ヒドラジン一水和物を9.2g及びジエチレントリアミン1.9gを水33.1gに溶解したポリアミン水溶液を添加し、40±5℃で90分間攪拌した後、減圧下に40℃で脱溶剤(脱メチルエチルケトン)を行い、得量:1kg、ポリウレタン不揮発:35.0%、の水系ポリウレタン組成物Aを得た。
[Synthetic Example of Aqueous Polyurethane Resin Contained in Antiviral Agent Composition of the Present Invention]
(Synthesis Example 1)
251.9 g of 1,6-hexanediol polycarbonate polyol (molecular weight 1,000) and 10.3 g of DMPA (dimethylol propionic acid) in a four-necked flask equipped with a stirrer, a reflux cooling tube, a thermometer and a nitrogen blowing tube. , 1,4-BD (butanediol) 3.4 g, methyl ethyl ketone 114.5 g as a solvent, weighed and mixed uniformly, then HDI (hexamethylene diisocyanate) 77.0 g as a polyisocyanate was added, and 80 ± 5 ° C. For 180 minutes, a methyl ethyl ketone solution of a terminal isocyanate group-containing urethane prepolymer having an isocyanate group content of 1.68% by mass was obtained. Then, 7.3 g of triethylamine is added at 60 ° C. to carry out a neutralization reaction. Next, 643.2 g of water was gradually added and stirred to emulsify and disperse the terminal isocyanate group-containing urethane prepolymer. To this emulsion dispersion, an aqueous polyamine solution prepared by dissolving 9.2 g of hydrazine monohydrate and 1.9 g of diethylenetriamine in 33.1 g of water was added, and the mixture was stirred at 40 ± 5 ° C. for 90 minutes and then at 40 ° C. under reduced pressure. The solvent was removed (demethylethylketone) to obtain an aqueous polyurethane composition A having a obtained amount of 1 kg and a polyurethane non-volatile: 35.0%.
(合成例2)
攪拌機、還流冷却管、温度計及び窒素吹込み管を備えた4ツ口フラスコに、1,6−ヘキサンジオールポリカーボネートポリオール(分子量1,000)230.0g、DMPA(ジメチロールプロピオン酸)10.3g、1,4−BD(ブタンジオール)3.5g、溶媒としてメチルエチルケトン 114.0gを量り取り、均一に混合した後、ポリイソシアネートとしてとしてHDI(ヘキサメチレンジイソシアネート)96.9gを加え、80±5℃で180分間反応させ、イソシアネート基の含有量が4.26質量%である末端イソシアネート基含有ウレタンプレポリマーのメチルエチルケトン溶液を得た。その後60℃でトリエチルアミン7.4gを加え中和反応を行う。次に水640.2gを徐々に加えて攪拌し、前記末端イソシアネート基含有ウレタンプレポリマーを乳化分散させた。この乳化分散液に、ヒドラジン一水和物を11.5g及びジエチレントリアミン2.4gを水41.7gに溶解したポリアミン水溶液を添加し、40±5℃で90分間攪拌した後、減圧下に40℃で脱溶剤(脱メチルエチルケトン)を行い、得量:1kg、ポリウレタン不揮発:35.0%、の水系ポリウレタン組成物Bを得た。
(Synthesis Example 2)
230.0 g of 1,6-hexanediol polycarbonate polyol (molecular weight 1,000) and 10.3 g of DMPA (dimethylol propionic acid) in a four-necked flask equipped with a stirrer, a reflux cooling tube, a thermometer and a nitrogen blowing tube. , 1,4-BD (butanediol) 3.5 g and methyl ethyl ketone 114.0 g as a solvent are weighed and mixed uniformly, and then HDI (hexamethylene diisocyanate) 96.9 g as a polyisocyanate is added and 80 ± 5 ° C. For 180 minutes, a methyl ethyl ketone solution of a terminal isocyanate group-containing urethane prepolymer having an isocyanate group content of 4.26% by mass was obtained. Then, at 60 ° C., 7.4 g of triethylamine is added to carry out a neutralization reaction. Next, 640.2 g of water was gradually added and stirred to emulsify and disperse the terminal isocyanate group-containing urethane prepolymer. To this emulsion dispersion, an aqueous polyamine solution prepared by dissolving 11.5 g of hydrazine monohydrate and 2.4 g of diethylenetriamine in 41.7 g of water was added, and the mixture was stirred at 40 ± 5 ° C. for 90 minutes and then at 40 ° C. under reduced pressure. The solvent was removed (demethylethylketone) to obtain an aqueous polyurethane composition B having a obtained amount of 1 kg and a polyurethane non-volatile: 35.0%.
(合成例3)
攪拌機、還流冷却管、温度計及び窒素吹込み管を備えた4ツ口フラスコに、1,6−ヘキサンジオールポリカーボネートポリオール(分子量1,000)263.2g、DMPA(ジメチロールプロピオン酸)5.1g、1,4−BD(ブタンジオール)3.4g、溶媒としてメチルエチルケトン 114.4gを量り取り、均一に混合した後、ポリイソシアネートとしてとしてHDI(ヘキサメチレンジイソシアネート)71.4gを加え、80±5℃で180分間反応させ、イソシアネート基の含有量が1.56質量%である末端イソシアネート基含有ウレタンプレポリマーのメチルエチルケトン溶液を得た。その後60℃でトリエチルアミン3.7gを加え中和反応を行う。次に水639.7gを徐々に加えて攪拌し、前記末端イソシアネート基含有ウレタンプレポリマーを乳化分散させた。この乳化分散液に、ヒドラジン一水和物を8.5g及びジエチレントリアミン1.8gを水30.7gに溶解したポリアミン水溶液を添加し、40±5℃で90分間攪拌した後、減圧下に40℃で脱溶剤(脱メチルエチルケトン)を行い、得量:1kg、ポリウレタン不揮発:35.0%、の水系ポリウレタン組成物Cを得た。
(Synthesis Example 3)
263.2 g of 1,6-hexanediol polycarbonate polyol (molecular weight 1,000) and 5.1 g of DMPA (dimethylol propionic acid) in a four-necked flask equipped with a stirrer, a reflux cooling tube, a thermometer and a nitrogen blowing tube. , 1,4-BD (butanediol) 3.4 g, methyl ethyl ketone 114.4 g as a solvent are weighed and mixed uniformly, then HDI (hexamethylene diisocyanate) 71.4 g as a polyisocyanate is added, and 80 ± 5 ° C. For 180 minutes, a methyl ethyl ketone solution of a terminal isocyanate group-containing urethane prepolymer having an isocyanate group content of 1.56% by mass was obtained. Then, 3.7 g of triethylamine is added at 60 ° C. to carry out a neutralization reaction. Next, 639.7 g of water was gradually added and stirred to emulsify and disperse the terminal isocyanate group-containing urethane prepolymer. To this emulsion dispersion, an aqueous polyamine solution prepared by dissolving 8.5 g of hydrazine monohydrate and 1.8 g of diethylenetriamine in 30.7 g of water was added, and the mixture was stirred at 40 ± 5 ° C. for 90 minutes and then at 40 ° C. under reduced pressure. The solvent was removed (demethylethylketone) to obtain an aqueous polyurethane composition C having a obtained amount of 1 kg and a polyurethane non-volatile: 35.0%.
(合成例4)
攪拌機、還流冷却管、温度計及び窒素吹込み管を備えた4ツ口フラスコに、1,6−ヘキサンジオールポリカーボネートポリオール(分子量3,000)287.4g、DMPA(ジメチロールプロピオン酸)10.2g、1,4−BD(ブタンジオール)3.4g、溶媒としてメチルエチルケトン 115.2gを量り取り、均一に混合した後、ポリイソシアネートとしてとしてHDI(ヘキサメチレンジイソシアネート)44.1gを加え、80±5℃で180分間反応させ、イソシアネート基の含有量が0.96質量%である末端イソシアネート基含有ウレタンプレポリマーのメチルエチルケトン溶液を得た。その後60℃でトリエチルアミン7.3gを加え中和反応を行う。次に水647.2gを徐々に加えて攪拌し、前記末端イソシアネート基含有ウレタンプレポリマーを乳化分散させた。この乳化分散液に、エチレンジアミンを3.8g及びジエチレントリアミン1.1gを水14.6gに溶解したポリアミン水溶液を添加し、40±5℃で90分間攪拌した後、減圧下に40℃で脱溶剤(脱メチルエチルケトン)を行い、得量:1kg、ポリウレタン不揮発:35.0%、の水系ポリウレタン組成物Dを得た。
(Synthesis Example 4)
287.4 g of 1,6-hexanediol polycarbonate polyol (molecular weight 3,000) and 10.2 g of DMPA (dimethylol propionic acid) in a four-necked flask equipped with a stirrer, a reflux cooling tube, a thermometer and a nitrogen blowing tube. , 1,4-BD (butanediol) 3.4 g, methyl ethyl ketone 115.2 g as a solvent were weighed and mixed uniformly, and then 44.1 g of HDI (hexamethylene diisocyanate) as a polyisocyanate was added, and the temperature was 80 ± 5 ° C. For 180 minutes, a methyl ethyl ketone solution of a terminal isocyanate group-containing urethane prepolymer having an isocyanate group content of 0.96% by mass was obtained. Then, 7.3 g of triethylamine is added at 60 ° C. to carry out a neutralization reaction. Next, 647.2 g of water was gradually added and stirred to emulsify and disperse the terminal isocyanate group-containing urethane prepolymer. To this emulsion dispersion, an aqueous polyamine solution prepared by dissolving 3.8 g of ethylenediamine and 1.1 g of diethylenetriamine in 14.6 g of water was added, and the mixture was stirred at 40 ± 5 ° C. for 90 minutes and then desolvated at 40 ° C. under reduced pressure. Demethylethyl ketone) was carried out to obtain an aqueous polyurethane composition D having a yield of 1 kg and a polyurethane non-volatile substance of 35.0%.
(合成例5)
攪拌機、還流冷却管、温度計及び窒素吹込み管を備えた4ツ口フラスコに、1,6−ヘキサンジオールポリカーボネートポリオール(分子量3,000)207.2g、DMPA(ジメチロールプロピオン酸)41.6g、1,4−BD(ブタンジオール)3.5g、溶媒としてメチルエチルケトン 113.6gを量り取り、均一に混合した後、ポリイソシアネートとしてとしてHDI(ヘキサメチレンジイソシアネート)88.0gを加え、80±5℃で180分間反応させ、イソシアネート基の含有量が1.94質量%である末端イソシアネート基含有ウレタンプレポリマーのメチルエチルケトン溶液を得た。その後60℃でトリエチルアミン29.8gを加え中和反応を行う。次に水664.6gを徐々に加えて攪拌し、前記末端イソシアネート基含有ウレタンプレポリマーを乳化分散させた。この乳化分散液に、エチレンジアミンを7.6g及びジエチレントリアミン2.2gを水29.1gに溶解したポリアミン水溶液を添加し、40±5℃で90分間攪拌した後、減圧下に40℃で脱溶剤(脱メチルエチルケトン)を行い、得量:1kg、ポリウレタン不揮発:35.0%、の水系ポリウレタン組成物Eを得た。
(Synthesis Example 5)
207.2 g of 1,6-hexanediol polycarbonate polyol (molecular weight 3,000) and 41.6 g of DMPA (dimethylol propionic acid) in a four-necked flask equipped with a stirrer, a reflux cooling tube, a thermometer and a nitrogen blowing tube. , 1,4-BD (butanediol) 3.5 g and methyl ethyl ketone 113.6 g as a solvent are weighed and mixed uniformly, and then 88.0 g of HDI (hexamethylene diisocyanate) as a polyisocyanate is added and 80 ± 5 ° C. For 180 minutes, a methyl ethyl ketone solution of a terminal isocyanate group-containing urethane prepolymer having an isocyanate group content of 1.94% by mass was obtained. Then, 29.8 g of triethylamine is added at 60 ° C. to carry out a neutralization reaction. Next, 664.6 g of water was gradually added and stirred to emulsify and disperse the terminal isocyanate group-containing urethane prepolymer. To this emulsion dispersion, an aqueous polyamine solution prepared by dissolving 7.6 g of ethylenediamine and 2.2 g of diethylenetriamine in 29.1 g of water was added, and the mixture was stirred at 40 ± 5 ° C. for 90 minutes and then desolvated at 40 ° C. under reduced pressure. Demethylethyl ketone) was carried out to obtain an aqueous polyurethane composition E having a yield of 1 kg and a polyurethane non-volatile substance of 35.0%.
(合成例6)
攪拌機、還流冷却管、温度計及び窒素吹込み管を備えた4ツ口フラスコに、1,6−ヘキサンジオールポリカーボネートポリオール(分子量1,000)170.5g、1,6−ヘキサンジオール/テレフタル酸ポリエステルポリオール(分子量1,000)80.6g、DMPA(ジメチロールプロピオン酸)10.5g、1,4−BD(ブタンジオール)3.5g、溶媒としてメチルエチルケトン 114.2gを量り取り、均一に混合した後、ポリイソシアネートとしてとしてHDI(ヘキサメチレンジイソシアネート)77.5gを加え、80±5℃で180分間反応させ、イソシアネート基の含有量が1.69質量%である末端イソシアネート基含有ウレタンプレポリマーのメチルエチルケトン溶液を得た。その後60℃でトリエチルアミン7.5gを加え中和反応を行う。次に水643.2gを徐々に加えて攪拌し、前記末端イソシアネート基含有ウレタンプレポリマーを乳化分散させた。この乳化分散液に、ヒドラジン一水和物を9.2g及びジエチレントリアミン1.9gを水33.3gに溶解したポリアミン水溶液を添加し、40±5℃で90分間攪拌した後、減圧下に40℃で脱溶剤(脱メチルエチルケトン)を行い、得量:1kg、ポリウレタン不揮発:35.0%、の水系ポリウレタン組成物Fを得た。
(Synthesis Example 6)
170.5 g of 1,6-hexanediol polycarbonate polyol (molecular weight 1,000), 1,6-hexanediol / polyester terephthalate in a four-necked flask equipped with a stirrer, a reflux cooling tube, a thermometer and a nitrogen blowing tube. After weighing 80.6 g of polyol (molecular weight 1,000), 10.5 g of DMPA (dimethylol propionic acid), 3.5 g of 1,4-BD (butanediol), and 114.2 g of methyl ethyl ketone as a solvent and mixing them uniformly. , HDI (hexamethylene diisocyanate) 77.5 g as a polyisocyanate is added and reacted at 80 ± 5 ° C. for 180 minutes, and a methyl ethyl ketone solution of a terminal isocyanate group-containing urethane prepolymer having an isocyanate group content of 1.69% by mass. Got Then, 7.5 g of triethylamine is added at 60 ° C. to carry out a neutralization reaction. Next, 643.2 g of water was gradually added and stirred to emulsify and disperse the terminal isocyanate group-containing urethane prepolymer. To this emulsion dispersion, an aqueous polyamine solution prepared by dissolving 9.2 g of hydrazine monohydrate and 1.9 g of diethylenetriamine in 33.3 g of water was added, and the mixture was stirred at 40 ± 5 ° C. for 90 minutes and then at 40 ° C. under reduced pressure. The solvent was removed (demethylethylketone) to obtain an aqueous polyurethane composition F having a obtained amount of 1 kg and a polyurethane non-volatile: 35.0%.
(比較合成例1)
攪拌機、環流冷却管、温度計及び窒素導入管を付した四つ口フラスコに、1,6−ヘキサンジオールポリカーボネートポリオール(平均分子量1000)244.2g、トリメチロールプロパン4.7g、ジブチル錫ジラウレート0.099g及びメチルエチルケトン150gを仕込み、均一に混合した後、H12MDI(ジシクロヘキシルメタンジイソシアネート)97.1gを加え、80℃で300分間反応させ、イソシアネート基の含有量が1.26質量%である末端イソシアネート基含有ウレタンプレポリマーのメチルエチルケトン溶液を得た。
前記溶液を30℃以下に冷却してデシルリン酸エステル0.3g及びポリオキシエチレントリスチリルフェニルエーテル(HLB=15)15.0gを添加し、均一に混合した後、ディスパー羽根を用いて水638.7gを徐々に加え転相乳化、分散を行い分散液を得た。そして、ピペラジン6水和物4.8gと、ジエチレントリアミン1.9gを水20.2gに溶解したポリアミン水溶液を前記分散液に添加し、90分間鎖伸長反応させた後、減圧下、35℃にて脱溶剤を行い、得量:1kg、ポリウレタン不揮発分35.0質量%の水系ポリウレタン組成物Gを得た。
(Comparative Synthesis Example 1)
In a four-necked flask equipped with a stirrer, a recirculation cooling tube, a thermometer and a nitrogen introduction tube, 244.2 g of 1,6-hexanediol polycarbonate polyol (average molecular weight 1000), 4.7 g of trimethylolpropane, and dibutyltin dilaurate 0. After charging 099 g and 150 g of methyl ethyl ketone and mixing them uniformly, 97.1 g of H12MDI (dicyclohexylmethanediisocyanate) was added and reacted at 80 ° C. for 300 minutes to contain a terminal isocyanate group having an isocyanate group content of 1.26% by mass. A methyl ethyl ketone solution of urethane prepolymer was obtained.
The solution was cooled to 30 ° C. or lower, 0.3 g of decyl phosphate ester and 15.0 g of polyoxyethylene tristyrylphenyl ether (HLB = 15) were added, and the mixture was uniformly mixed. 7 g was gradually added, and phase inversion emulsification and dispersion were carried out to obtain a dispersion. Then, an aqueous polyamine solution prepared by dissolving 4.8 g of piperazine hexahydrate and 1.9 g of diethylenetriamine in 20.2 g of water was added to the dispersion solution, followed by a chain extension reaction for 90 minutes, and then at 35 ° C. under reduced pressure. The solvent was removed to obtain an aqueous polyurethane composition G having a obtained amount of 1 kg and a polyurethane non-volatile content of 35.0% by mass.
以下の表1には、上記の合成例1〜6及び比較合成例1で得られた水系ポリウレタン組成物におけるCOO基の量、NCO/OH比、ポリオールの種類が要約されている。
表中のPCDはポリカーボネートジオールを、PEDはポリエステルジオールを示している。
Table 1 below summarizes the amount of COO groups, NCO / OH ratio, and type of polyol in the water-based polyurethane compositions obtained in Synthesis Examples 1 to 6 and Comparative Synthesis Example 1 above.
In the table, PCD indicates polycarbonate diol and PED indicates polyester diol.
(アクリル組成物合成例1)
温度計、撹拌機、滴下装置、還流冷却管及び窒素導入管を備えた反応装置に、イオン交換水28部を秤量し、窒素を封入して内温を80℃まで昇温させた。そして、その温度に保ちながら、10%濃度の過硫酸アンモニウム水溶液2部を添加し、直ちに、別に準備しておいた、下記のようにして調製した単量体乳化物を連続的に4時間滴下して乳化重合した。上記で用いた単量体乳化物は、アクリル酸32部、アクリル酸エチル45部、アクリル酸ブチル23部の単量体混合物に、ポリオキシエチレンアルキルエーテル硫酸ナトリウム(花王株式会社製、商品名:ラテムルE−118B)4部とイオン交換水30部を混合し、乳化することで調製した。また、この単量体乳化物の滴下に並行して、5%濃度の過硫酸アンモニウム水溶液4部を滴下した。滴下終了後、80℃で4時間熟成し、その後、室温まで冷却した。最後に、アンモニア水で中和し、固形分を水で調整して、固形分60%である水系アクリル組成物aを得た。
(Acrylic Composition Synthesis Example 1)
28 parts of ion-exchanged water was weighed in a reaction device equipped with a thermometer, a stirrer, a dropping device, a reflux condenser and a nitrogen introduction tube, and nitrogen was sealed to raise the internal temperature to 80 ° C. Then, while maintaining the temperature, 2 parts of a 10% aqueous solution of ammonium persulfate was added, and immediately, a separately prepared monomeric emulsion prepared as described below was continuously added dropwise for 4 hours. Emulsified and polymerized. The monomer emulsion used above is a monomer mixture of 32 parts of acrylic acid, 45 parts of ethyl acrylate, and 23 parts of butyl acrylate, and sodium polyoxyethylene alkyl ether sulfate (manufactured by Kao Co., Ltd., trade name: It was prepared by mixing 4 parts of Latemul E-118B) and 30 parts of ion-exchanged water and emulsifying them. Further, in parallel with the dropping of the monomer emulsion, 4 parts of a 5% concentration ammonium persulfate aqueous solution was dropped. After completion of the dropping, the mixture was aged at 80 ° C. for 4 hours, and then cooled to room temperature. Finally, the mixture was neutralized with aqueous ammonia and the solid content was adjusted with water to obtain an aqueous acrylic composition a having a solid content of 60%.
(アクリル組成物合成例2)
メタクリル酸メチル25部、アクリル酸ブチル75部を単量体混合物とすること以外は、上記アクリル組成物合成例1と同様にして、水系アクリル組成物bを得た。
(Acrylic Composition Synthesis Example 2)
An aqueous acrylic composition b was obtained in the same manner as in the above acrylic composition synthesis example 1 except that 25 parts of methyl methacrylate and 75 parts of butyl acrylate were used as a monomer mixture.
(分散剤合成例1)
温度計、窒素導入管および高粘度用攪拌機を付した容量1000mlの4つ口フラスコに、ポリエチレングリコール6000(分子量6000)を500部、n−ドデシルアルコールにエチレンオキサイドを5モル付加したポリエーテルモノオールを13.5部入れ低圧下(500〜1500Pa)にて80〜90℃で3時間脱水し、系の水分含量を0.03%とした。ついで70℃に冷却し、ヘキサメチレンジイソシアネートを16.8部加え、窒素気流下85〜90℃でイソシアネート含量が0%になるまで反応させ(3時間)、室温にて冷却後淡黄色粘稠固体のウレタン変性ポリエーテルcを得た。
(Dispersant Synthesis Example 1)
500 parts of polyethylene glycol 6000 (molecular weight 6000) and 5 mol of ethylene oxide added to n-dodecyl alcohol in a 4-port flask with a capacity of 1000 ml equipped with a thermometer, a nitrogen introduction tube and a stirrer for high viscosity. Was put in 13.5 parts and dehydrated under low pressure (500 to 1500 Pa) at 80 to 90 ° C. for 3 hours to bring the water content of the system to 0.03%. Then, the mixture was cooled to 70 ° C., 16.8 parts of hexamethylene diisocyanate was added, and the mixture was reacted at 85 to 90 ° C. under a nitrogen stream until the isocyanate content became 0% (3 hours), cooled at room temperature, and then a pale yellow viscous solid. Urethane-modified polyether c was obtained.
表2〜4に示す各組成物(実施例1〜28及び比較例1〜11)を調整し、抗ウイルス剤組成物とした。ただし、抗ウイルス剤(メトキシシラン系第4級アンモニウム塩)の添加順は必ず調整の最後に行うものとする。 Each composition shown in Tables 2 to 4 (Examples 1 to 28 and Comparative Examples 1 to 11) was prepared to prepare an antiviral agent composition. However, the order of addition of the antiviral agent (methoxysilane quaternary ammonium salt) must be performed at the end of the adjustment.
次に、調製した各種抗ウイルス剤組成物について、液安定性、キワツキ性、呈色性、風合い、耐摩耗性、難燃性に関する評価試験結果を示す。
評価試験に用いた各材料は以下の通りである。
1.抗ウイルス剤:3−(トリメトキシシリル)プロピルジメチルオクタデシルアンモニウムクロライドのメタノール溶液
Next, the evaluation test results regarding liquid stability, fluffiness, coloration, texture, abrasion resistance, and flame retardancy of the prepared various antiviral agent compositions are shown.
The materials used in the evaluation test are as follows.
1. 1. Antiviral agent: Methanol solution of 3- (trimethoxysilyl) propyldimethyloctadecylammonium chloride
2.添加剤:
・フィラー:ACEMATT TS−100(Evonik Industries AG製、平均粒子径:10μm)
・消泡剤:フォームレックス747(日華化学株式会社製)
・レベリング剤:ディスパロン AQ−7120(楠本化成株式会社製)
2. Additive:
-Filler: ACEMATT TS-100 (manufactured by Evonik Industries AG, average particle size: 10 μm)
・ Defoamer: Foam Rex 747 (manufactured by NICCA CHEMICAL CO., LTD.)
-Leveling agent: Disparon AQ-7120 (manufactured by Kusumoto Kasei Co., Ltd.)
3.分散剤:
・ウレタン変性ポリエーテルI:ネオステッカー N(日華化学株式会社製)
・ウレタン変性ポリエーテルII:SNシックナー603(サンノプコ株式会社製)
・ウレタン変性ポリエーテルIII:エレミノールN62(三洋化成工業株式会社製)
・キサンタンガム:KELZAN(三晶株式会社製)
3. 3. Dispersant:
・ Urethane-modified polyether I: Neo Sticker N (manufactured by NICCA CHEMICAL CO., LTD.)
-Urethane modified polyether II: SN thickener 603 (manufactured by San Nopco Ltd.)
-Urethane-modified polyether III: Eleminor N62 (manufactured by Sanyo Chemical Industries, Ltd.)
・ Xanthan gum: KELZAN (manufactured by Sansho Co., Ltd.)
[液安定性(相溶性)試験]
各組成物について、調製後の組成物中の樹脂カスの有無を目視により判断し、◎(樹脂カス発生無し)、○(樹脂カス発生わずかに有り)、△(樹脂カス発生有り)、×(多量の樹脂カス発生有り)の評価基準にて評価し、○以上で合格とした。
上記の評価結果を表2〜4に示す。
[Liquid stability (compatibility) test]
For each composition, the presence or absence of resin residue in the prepared composition is visually judged, and ◎ (no resin residue is generated), ○ (slight resin residue is generated), △ (resin residue is generated), × ( Evaluation was made according to the evaluation criteria (with a large amount of resin residue generated), and a score of ○ or higher was considered acceptable.
The above evaluation results are shown in Tables 2-4.
[抗ウイルス剤の固定化処理]
布帛に関しては、質量390g/m2のポリエステル原布に染色と同時に、浴中難燃剤としてリン酸エステルアミド6%owfしたものに、表2〜4に示す各組成物をPic-up率約60%で、dip-nip後に150℃で2.5分乾燥を行った。
又、ポリ塩化ビニルシート(商品名:ランチャール)については、当該シートの表面に、表面ベース処理層として、ポリウレタン樹脂を20g/m2となるよう均一に塗布した後、120℃で2分乾燥を行い、その後、表2〜4に示す各組成物を20g/m2となるよう均一に塗布した後、150℃で2.5分乾燥を行い、抗ウイルス剤の固定化処理を行った。
更に、ウレタン合皮ポリウレタンシート(商品名:レザーフレクシード)については、当該シートの表面に、表2〜4に示す各組成物を20g/m2となるよう均一に塗布した後、150℃で2.5分乾燥を行い、抗ウイルス剤の固定化処理を行った。
[Immobilization treatment of antiviral agents]
Regarding the cloth, a polyester raw cloth having a mass of 390 g / m 2 was dyed, and at the same time, 6% owf of phosphate ester amide was applied as a flame retardant in the bath, and each composition shown in Tables 2 to 4 was added to a Pic-up rate of about 60. After dip-nip, it was dried at 150 ° C. for 2.5 minutes.
For a polyvinyl chloride sheet (trade name: Launchard), a polyurethane resin is uniformly applied to the surface of the sheet as a surface base treatment layer so as to be 20 g / m 2, and then dried at 120 ° C. for 2 minutes. After that, each composition shown in Tables 2 to 4 was uniformly applied so as to be 20 g / m 2, and then dried at 150 ° C. for 2.5 minutes to immobilize the antiviral agent.
Further, for the urethane synthetic leather polyurethane sheet (trade name: leather flexseed), each composition shown in Tables 2 to 4 is uniformly applied to the surface of the sheet so as to be 20 g / m 2, and then at 150 ° C. After drying for 2.5 minutes, an antiviral agent was immobilized.
[キワツキ性の評価]
上記の固定化処理を行ったポリウレタンシート、ポリ塩化ビニルシート、布帛の表面に、蒸留水を1ml滴下し、乾燥後のキワツキを目視により評価した。表2〜4には上記の結果が示されており、評価基準については以下の通りである。
尚、上記の液安定性試験において十分な相溶性を有さない組成物については、キワツキ性の評価は実施しなかった。
◎:キワツキが全く観察されない
〇:キワツキがほとんど観察されない
△:キワツキが観察される
×:目立ったキワツキが観察される
○以上で合格とした。
[Evaluation of fluffiness]
1 ml of distilled water was added dropwise to the surfaces of the polyurethane sheet, the polyvinyl chloride sheet, and the fabric subjected to the above-mentioned immobilization treatment, and the dryness was visually evaluated. The above results are shown in Tables 2 to 4, and the evaluation criteria are as follows.
In the above liquid stability test, no evaluation of the fluffiness was carried out for the composition which did not have sufficient compatibility.
⊚: No wrinkles are observed 〇: Almost no wrinkles are observed Δ: No wrinkles are observed ×: Conspicuous wrinkles are observed ○ The above is acceptable.
[呈色性の評価]
布帛に付着した抗ウイルス剤の検出には、ブロモフェノールブルーとアンモニウム塩とのカチオン性の呈色反応を用いた。具体的には、抗ウイルス剤の固定処理後の布帛、又は、ポリウレタンシート、又は、ポリ塩化ビニルシートについて5cm×5cmのサンプル片を切り出し、ブロモフェノールブルーの呈色反応(反応剤濃度:0.03%sol、反応時間:180秒)を行い、乾燥した後、呈色前後の試験片を分光光度計(コニカミノルタ社製)にて測定し、ΔEを算出した。測定及び算出方法は、JISZ8781(2012)に準じた。
○:ΔE≧10
△:5≦ΔE<10
×:ΔE<5
○で合格とした。
[Evaluation of color development]
A cationic color reaction between bromophenol blue and an ammonium salt was used to detect the antiviral agent adhering to the fabric. Specifically, a 5 cm × 5 cm sample piece was cut out from the cloth, the polyurethane sheet, or the polyvinyl chloride sheet after the immobilization treatment of the antiviral agent, and the color reaction of bromophenol blue (reactant concentration: 0. 03% sol, reaction time: 180 seconds), and after drying, the test pieces before and after coloration were measured with a spectrophotometer (manufactured by Konica Minolta) to calculate ΔE. The measurement and calculation method was based on JISZ8781 (2012).
◯: ΔE ≧ 10
Δ: 5 ≦ ΔE <10
X: ΔE <5
Passed with ○.
[風合いの評価]
3:柔軟な風合い
2:やや柔軟な風合い
1:粗硬な風合い
[Evaluation of texture]
3: Flexible texture 2: Slightly flexible texture 1: Coarse and hard texture
[耐摩耗性の評価]
抗ウイルス剤の固定処理後のポリウレタンシート、ポリ塩化ビニルシートについて、平面摩耗試験機を用い、0.9kgの加重で綿帆布(JIS L 3102(1954)の6号)により10,000回の摩耗を行った後、試験片の状態を以下の基準に従い評価を行った。
◎:損傷なし
○:わずかに損傷している
×:激しく損傷している
[Evaluation of wear resistance]
The polyurethane sheet and polyvinyl chloride sheet after fixing the antiviral agent are worn 10,000 times with a cotton canvas (JIS L 3102 (1954) No. 6) under a load of 0.9 kg using a flat surface wear tester. After that, the condition of the test piece was evaluated according to the following criteria.
◎: No damage ○: Slightly damaged ×: Severely damaged
[難燃性の評価]
FMVSS−302(米国自動車安全基準)JIS D 1201[1973年制定]に従い燃焼速度を布帛10枚について測定した。10枚の燃焼速度の平均値(算術平均値)を、以下の基準に従い判定した。
◎:燃焼速度の平均値が50mm/分より遅い、もしくは燃焼距離が50mm以下かつ燃焼時間が60秒以内
○:燃焼速度の平均値が50mm/分以上、かつ、100mm/分未満
×;燃焼速度の平均値が100mm/分以上
[Evaluation of flame retardancy]
The burning rate was measured for 10 fabrics according to FMVSS-302 (Federal Motor Vehicle Safety Standards) JIS D 1201 [established in 1973]. The average value (arithmetic mean value) of the burning rates of 10 sheets was determined according to the following criteria.
⊚: The average value of the combustion rate is slower than 50 mm / min, or the combustion distance is 50 mm or less and the combustion time is within 60 seconds. ○: The average value of the combustion rate is 50 mm / min or more and less than 100 mm / min ×; Average value of 100 mm / min or more
上記の表2に示されるとおり、分散剤として、水溶性有機高分子の1種であるウレタン変性ポリエーテルとキサンタンガムの少なくともいずれか一方を含む組成を有する実施例1〜8の組成物の場合には、樹脂カスが発生せず液安定性に優れ、処理後の布帛におけるキワツキ性は良好であった。
これに対して、分散剤であるウレタン変性ポリエーテルとキサンタンガムのいずれも含有しない比較例1の組成物の場合には液安定性が悪く、多量の樹脂カスが見られた。また、ポリウレタン組成物の代わりに、アクリル組成物を用いた比較例2の場合には、樹脂カスが見られ、呈色性も低い結果となり、燃焼性においても悪化する結果となった。COOH基を含まないポリウレタン組成物Gを用いる比較例3では、樹脂カスはなく液安定性は良好だが、呈色性が低い結果であった。
ウレタン変性ポリエーテルc、I、II、III、キサンタンガムを用いた、実施例1〜5の場合には、液安定性、キワツキ性、呈色性いずれも良好であった。
COOH%が0.5、1.0、4.0%であるポリウレタン組成物A、C、Eを含む実施例1、6,7の場合には、液安定性、キワツキ性、呈色性いずれも良好であった。
ポリカーボネートポリオールとポリエステルポリオールを併用したポリウレタン組成物Fを含む実施例8の場合には、液安定性、キワツキ性、呈色性いずれも良好であった。
As shown in Table 2 above, in the case of the compositions of Examples 1 to 8 having a composition containing at least one of urethane-modified polyether and xanthan gum, which is one kind of water-soluble organic polymer, as a dispersant. No resin residue was generated, the liquid stability was excellent, and the texture of the cloth after the treatment was good.
On the other hand, in the case of the composition of Comparative Example 1 containing neither the urethane-modified polyether as a dispersant nor xanthan gum, the liquid stability was poor and a large amount of resin residue was observed. Further, in the case of Comparative Example 2 in which the acrylic composition was used instead of the polyurethane composition, resin residue was observed, the coloration property was low, and the flammability was also deteriorated. In Comparative Example 3 in which the polyurethane composition G containing no COOH group was used, there was no resin residue and the liquid stability was good, but the color development was low.
In the cases of Examples 1 to 5 using urethane-modified polyethers c, I, II, III, and xanthan gum, liquid stability, fluffiness, and color development were all good.
In the case of Examples 1, 6 and 7 containing the polyurethane compositions A, C and E having a COOH% of 0.5, 1.0 and 4.0%, any of liquid stability, fluffiness and color development Was also good.
In the case of Example 8 containing the polyurethane composition F in which the polycarbonate polyol and the polyester polyol were used in combination, the liquid stability, the fluffiness, and the color development were all good.
上記の表3、4に示されるとおり、分散剤として、水溶性有機高分子の1種であるウレタン変性ポリエーテルとキサンタンガムの少なくともいずれか一方を含む組成を有する実施例9〜28の組成物の場合には、樹脂カスが発生せず液安定性に優れ、コーティング後のポリウレタンシート、またはポリ塩化ビニルシートにおけるキワツキ性、呈色性は良好であった。
これに対して、分散剤であるウレタン変性ポリエーテルとキサンタンガムのいずれも含有しない比較例4、8の組成物の場合には液安定性が悪く、多量の樹脂カスが見られた。また、ポリウレタン組成物の代わりに、COOH基を有するアクリル組成物aを用いた比較例5、9の場合には、液安定性が悪く樹脂カスが見られ、呈色性も悪かった。COOH基を有しないアクリル樹脂組成物bを用いた比較例6、10の場合には、液安定性は良好なものの、呈色性が悪かった。また、比較例5、6、9、10ではポリウレタンシート、またはポリ塩化ビニルシートとしての風合いが硬く耐摩耗性も悪かった。COOH基を有さないポリウレタン組成物Gを用いた比較例7、11では、キワツキ性と呈色性が悪く、ポリウレタンシート、またはポリ塩化ビニルシートとして耐摩耗性も悪かった。
ウレタン変性ポリエーテルc、I、II、IIIを用いた、実施例10〜13、20〜23の場合には、液安定性、キワツキ性、呈色性いずれも良好であった。
COOH%が0.5、1.0、4.0%、またはNCO/OH比が100/80〜100/60、またはポリオールの分子量が1000,3000と変化させたポリウレタン組成物A〜Eをそれぞれ含む実施例10、14〜17、20、24〜27の場合には、液安定性、キワツキ性、呈色性いずれも良好であった。
また、ウレタン変性ポリエーテル、キサンタンガムのいずれかを使用した実施例10、18、20、28の場合には、液安定性、キワツキ性、呈色性いずれも良好で、ウレタン変性ポリエーテルを用いた実施例10,20の場合にキワツキ性がより良好であった。
As shown in Tables 3 and 4 above, the compositions of Examples 9 to 28 having a composition containing at least one of urethane-modified polyether and xanthan gum, which is one of water-soluble organic polymers, as a dispersant. In the case, no resin residue was generated, the liquid stability was excellent, and the polyurethane sheet or the polyvinyl chloride sheet after coating had good fluffiness and color development.
On the other hand, in the case of the compositions of Comparative Examples 4 and 8 containing neither the urethane-modified polyether as a dispersant nor the xanthan gum, the liquid stability was poor and a large amount of resin residue was observed. Further, in the cases of Comparative Examples 5 and 9 in which the acrylic composition a having a COOH group was used instead of the polyurethane composition, the liquid stability was poor, resin residue was observed, and the color development property was also poor. In the cases of Comparative Examples 6 and 10 using the acrylic resin composition b having no COOH group, the liquid stability was good, but the color development was poor. Further, in Comparative Examples 5, 6, 9 and 10, the texture as a polyurethane sheet or a polyvinyl chloride sheet was hard and the abrasion resistance was also poor. In Comparative Examples 7 and 11 using the polyurethane composition G having no COOH group, the fluffiness and color development were poor, and the abrasion resistance as a polyurethane sheet or a polyvinyl chloride sheet was also poor.
In the cases of Examples 10 to 13 and 20 to 23 using urethane-modified polyethers c, I, II and III, the liquid stability, the fluffiness and the color development were all good.
Polyurethane compositions A to E in which the COOH% was changed to 0.5, 1.0, 4.0%, or the NCO / OH ratio was changed to 100/80 to 100/60, or the molecular weight of the polyol was changed to 1000, 3000, respectively. In the cases of Examples 10, 14 to 17, 20, 24 to 27, which included, the liquid stability, the fluffiness, and the color development were all good.
Further, in the cases of Examples 10, 18, 20 and 28 using either the urethane-modified polyether or the xanthan gum, the liquid stability, the fluffiness and the color-developing property were all good, and the urethane-modified polyether was used. In the case of Examples 10 and 20, the fluffiness was better.
本発明の抗ウイルス剤組成物は、表面にヒドロキシル基を持たない合成繊維等に対しても一度の加工で抗ウイルス剤を付与することができ、耐久性が優れた抗菌性および抗ウイルス性を有する布帛、ポリウレタンシート、ポリ塩化ビニルシートを製造するのに有用である。 The antiviral agent composition of the present invention can impart an antiviral agent to synthetic fibers and the like having no hydroxyl group on the surface in a single process, and has excellent antibacterial and antiviral properties. It is useful for producing cloths, polyurethane sheets, and polyvinyl chloride sheets.
Claims (8)
バインダーとしての、カルボキシル基及び/又はカルボキシレート基を有する水系ポリウレタン樹脂と、
を含む混合物であって、分散剤として水溶性有機高分子を含有することを特徴とする抗ウイルス剤組成物。 Antiviral agents containing methoxysilane quaternary ammonium salts,
An aqueous polyurethane resin having a carboxyl group and / or a carboxylate group as a binder, and
An antiviral agent composition comprising a water-soluble organic polymer as a dispersant.
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PCT/JP2022/001347 WO2022168577A1 (en) | 2021-02-08 | 2022-01-17 | Antiviral agent composition, antiviral fabric treated with said composition, antiviral polyurethane sheet, and antiviral polyvinyl chloride sheet |
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JP2006206839A (en) * | 2005-01-31 | 2006-08-10 | Nicca Chemical Co Ltd | Polyurethane resin water-based dispersion and manufacturing method of flame-retardant polyester fiber using the same |
JP2007045866A (en) * | 2005-08-08 | 2007-02-22 | Dai Ichi Kogyo Seiyaku Co Ltd | Aqueous polyurethane resin composition for nonporous film type moisture-permeable, waterproof finish and method for producing moisture-permeable, waterproof finish fabric |
WO2013047642A1 (en) * | 2011-09-29 | 2013-04-04 | Tbカワシマ株式会社 | Article comprising immobilized antibacterial agent and method for producing same |
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JP2006206839A (en) * | 2005-01-31 | 2006-08-10 | Nicca Chemical Co Ltd | Polyurethane resin water-based dispersion and manufacturing method of flame-retardant polyester fiber using the same |
JP2007045866A (en) * | 2005-08-08 | 2007-02-22 | Dai Ichi Kogyo Seiyaku Co Ltd | Aqueous polyurethane resin composition for nonporous film type moisture-permeable, waterproof finish and method for producing moisture-permeable, waterproof finish fabric |
WO2013047642A1 (en) * | 2011-09-29 | 2013-04-04 | Tbカワシマ株式会社 | Article comprising immobilized antibacterial agent and method for producing same |
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